{"id":11495,"date":"2018-04-18T08:00:35","date_gmt":"2018-04-18T12:00:35","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=11495"},"modified":"2026-04-17T21:18:49","modified_gmt":"2026-04-18T02:18:49","slug":"electrophilic-aromatic-substitutions-1-halogenation","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2018\/04\/18\/electrophilic-aromatic-substitutions-1-halogenation\/","title":{"rendered":"Electrophilic Aromatic Substitutions (1) &#8211; Halogenation of Benzene"},"content":{"rendered":"<p><strong>Halogenation of Benzene via Electrophilic Aromatic Substitution<\/strong><\/p>\n<ul>\n<li>Unlike alkenes, benzene does <strong>not<\/strong> undergo rapid chlorination or bromination with Cl<sub>2<\/sub> or Br<sub>2<\/sub><\/li>\n<li>When it does undergo reaction with halogens, it occurs via\u00a0<strong>substitution<\/strong> instead of\u00a0<strong>addition;\u00a0<\/strong>a C-H bond on the aromatic ring breaks, and a C-X bond forms (where X is a halogen).<\/li>\n<li>This occurs via <strong>electrophilic aromatic substitution<\/strong>, with the rate limiting step being attack on the halogen electrophile by the aromatic ring. This generates a <strong>carbocation<\/strong> intermediate, which is quickly deprotonated to re-generate the aromatic ring.<\/li>\n<li>Halogenation can be made <strong>much more rapid<\/strong> by using a <strong>Lewis acid<\/strong> such as AlCl<sub>3<\/sub> or FeCl<sub>3<\/sub>. This accepts a lone pair from the halogen, making the halogen an even <strong>better<\/strong> electrophile.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-15904\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-halogenation-of-benzene-chlorination-and-bromination-of-benzene-with-lewis-acid-catalysis-fecl3.gif\" alt=\"summary halogenation of benzene chlorination and bromination of benzene with lewis acid catalysis fecl3\" width=\"600\" height=\"473\" \/><\/p>\n<p><span style=\"color: #993366;\"><em>[What about fluorine? If F<sub>2<\/sub>\u00a0wasn&#8217;t such a <a style=\"color: #993366;\" href=\"http:\/\/archive.is\/Q7Bvt\">ravenous beast<\/a>, we&#8217;d include it too, but as it stands, fluorine is best introduced to aromatic rings <a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/12\/03\/reactions-of-diazonium-salts-sandmeyer-and-related-reactions\/\">indirectly<\/a>]<\/em><\/span><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li class=\"p1\"><a href=\"#one\"><span class=\"s1\">Halogenation of Benzene <i>via<\/i> Electrophilic Aromatic Substitution<\/span><\/a><\/li>\n<li class=\"p1\"><a href=\"#two\"><span class=\"s1\">Lewis Acids Can Be Used To &#8220;Activate&#8221; Electrophiles<\/span><\/a><\/li>\n<li class=\"p1\"><a href=\"#three\">Electrophilic Chlorination of Benzene<\/a><\/li>\n<li class=\"p1\"><a href=\"#four\"><span class=\"s1\">Electrophilic Bromination of Benzene<\/span><\/a><\/li>\n<li class=\"p1\"><a href=\"#five\"><span class=\"s1\"><span class=\"s1\">Electrophilic Iodination of Benzene<\/span><\/span><\/a><\/li>\n<li class=\"p1\"><a href=\"#six\">Summary: Halogenation of Benzene<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quiz\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. Halogenation of Benzene <em>via<\/em> Electrophilic Aromatic Substitution<\/strong><\/h2>\n<p>Now that we&#8217;ve spent ample time digging into<\/p>\n<ul>\n<li>the <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/11\/09\/electrophilic-aromatic-substitution-the-mechanism\/\">mechanism of electrophilic aromatic substitution,\u00a0<\/a><\/li>\n<li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/09\/26\/activating-and-deactivating-groups-in-electrophilic-aromatic-substitution\/\">activating and deactivating groups<\/a>, and<\/li>\n<li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/02\/02\/understanding-ortho-para-meta-directors\/\"><em>ortho- ,para<\/em>&#8211; and <em>meta<\/em>&#8211; directors<\/a>,<\/li>\n<\/ul>\n<p>we&#8217;re finally ready to dig into some specific reactions in detail. First up: <strong>halogenation<\/strong>. How do we install Cl, Br, or I on an aromatic ring?<\/p>\n<p>You may recall that alkenes react readily with\u00a0 Cl<sub>2<\/sub>, Br<sub>2<\/sub>, and I<sub>2<\/sub>\u00a0to form dihalides.<\/p>\n<p>Benzene? Not so much. And when it does react with aromatic rings, it provides substitution rather than addition products.<\/p>\n<p><span style=\"color: #993366;\"><em>[Why? Recall that the <strong>resonance energy<\/strong> of benzene is about <strong>36 kcal\/mol,<\/strong> and electrophilic aromatic substitution disrupts aromaticity. ]<\/em><\/span><\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15905\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-halogenation-works-well-for-alkenes-but-benzene-is-not-reactive-enough-with-cl2-or-br2.gif\" alt=\"halogenation works well for alkenes but benzene is not reactive enough with cl2 or br2\" width=\"600\" height=\"409\" \/><\/p>\n<h2><strong><a id=\"two\"><\/a>2. Lewis Acids Can Be Used To &#8220;Activate&#8221; Electrophiles\u00a0<\/strong><\/h2>\n<p>Chlorine itself will react with &#8220;activated&#8221; benzene derivatives (such as phenol and aniline) but in order for chlorination to occur with electron-neutral or electron-poor aromatics, it needs a kick in the pants.<\/p>\n<p>This &#8220;kick in the pants&#8221; is provided by a Lewis acid.\u00a0 FeCl<sub>3<\/sub>\u00a0or AlCl<sub>3<\/sub> are the industry standard, but in practice many different Lewis acids can be employed.<\/p>\n<p>You may recall from the chapter on alcohols that protic acids are commonly used to turn poor electrophiles (e.g. alcohols) into better electrophiles by converting an alcohol into its conjugate acid.<em><span style=\"color: #993366;\"> [See article:<\/span> <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\">What Makes a Good Leaving Group<\/a>?]<\/em>.<\/p>\n<p>The &#8220;activated&#8221; alcohol is then able to participate in nucleophilic substitution or elimination reactions that it would not have been able to participate in otherwise:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15906\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-lewis-acids-activate-electrophiles-the-conjugate-acid-is-a-better-electrophile.gif\" alt=\"lewis acids activate electrophiles the conjugate acid is a better electrophile\" width=\"630\" height=\"298\" \/><\/p>\n<p><span style=\"color: #993366;\"><em>[The leaving group may even depart entirely to give a carbocation, an even better electrophile!]<\/em><\/span><\/p>\n<p>In much the same way, coordination of the Lewis acid to one of the chlorines converts it into an even <strong>better leaving group<\/strong>, with the net effect of <strong>weakening<\/strong> the Cl-Cl bond. Attack on the terminal Cl by a nucleophile results in the loss of [Cl-FeCl<sub>3<\/sub>]<sup>&#8211;<\/sup> , an even <strong>better<\/strong> leaving group than Cl<sup>&#8211;<\/sup> .<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15907\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-lewis-acids-like-fecl3-make-halogens-into-better-leaving-groups-since-fecl4-is-a-weaker-base-than-cl-.gif\" alt=\"lewis acids like fecl3 make halogens into better leaving groups since fecl4 is a weaker base than cl-\" width=\"630\" height=\"241\" \/><\/p>\n<p>Sometimes we draw this as an equilibrium.\u00a0 Textbooks vary. I personally prefer showing the intact Cl\u2013Cl bond.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15908\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-equilibrium-between-fecl3-complex-with-cl2-chloronium-ion.gif\" alt=\"equilibrium between fecl3 complex with cl2 chloronium ion\" width=\"600\" height=\"213\" \/><\/p>\n<h2><strong><a id=\"three\"><\/a>3. Electrophilic Chlorination of Benzene<\/strong><\/h2>\n<p>This &#8220;activated&#8221; electrophile can then be attacked by the <strong>nucleophile<\/strong> (the benzene ring) in an electrophilic aromatic substitution reaction. Here, <strong>C-Cl forms<\/strong>, and the <strong>C-C (pi) bond breaks<\/strong>!<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15909\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-electrophilic-aromatic-substitution-of-benzene-chlorination-mechanism-step-1-attack-on-cl.gif\" alt=\"electrophilic aromatic substitution of benzene chlorination mechanism step 1 attack on cl\" width=\"600\" height=\"210\" \/><\/p>\n<p>In the next step,\u00a0 a weak base removes a proton from the carbocation intermediate, <strong>breaking C-H<\/strong> and<strong> forming C-C (pi)<\/strong>.<\/p>\n<p>If this looks a tiny bit familiar, that&#8217;s because this second step greatly resembles the second step in the <strong>E1 reaction.<\/strong>\u00a0 As in the E1, only a very weak base is required to remove a proton adjacent to a carbocation.\u00a0 The chloride ion (Cl<sup>&#8211;\u00a0<\/sup>) will do.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15910\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-electrophilic-aromatic-substitution-of-benzene-cl2-step-2-deprotonation.gif\" alt=\"electrophilic aromatic substitution of benzene cl2 step 2 deprotonation\" width=\"600\" height=\"204\" \/><\/p>\n<p><span style=\"color: #993366;\"><em>[Note: there are a lot of different ways to draw this, I&#8217;ve only shown one. See <a style=\"color: #993366;\" href=\"#noteone\">Note 1<\/a>].<\/em><\/span><\/p>\n<p>The final product here is chlorobenzene plus one equivalent of HCl. The FeCl<sub>3<\/sub>\u00a0 is then free to react with another equivalent of Cl<sub>2\u00a0<\/sub>. In other words, it behaves as a <strong>catalyst<\/strong> in this reaction.<\/p>\n<h2><a id=\"four\"><\/a>4. Electrophilic Bromination of Benzene<\/h2>\n<p>The same set of principles operate for electrophilic bromination. Here, the Lewis acids used are often FeBr<sub>3<\/sub> or AlBr<sub>3<\/sub>.<span style=\"color: #993366;\"> <em>[<a style=\"color: #993366;\" href=\"#notetwo\">Why not FeCl<sub>3<\/sub> or AlCl<sub>3<\/sub>?\u00a0 Note 2]<\/a><\/em><\/span><\/p>\n<p>The first step is activation of Br<sub>2<\/sub>, followed by attack and deprotonation, as before:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15911\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-electrophilic-aromatic-substitution-of-benzene-with-br2-and-febr3-full-mechanism.gif\" alt=\"electrophilic aromatic substitution of benzene with br2 and febr3 full mechanism\" width=\"600\" height=\"495\" \/><\/p>\n<p>It&#8217;s essentially the same reaction as chlorination except with the halogens swapped out.<\/p>\n<h2><strong><a id=\"five\"><\/a>5. Electrophilic Iodination of Benzene<\/strong><\/h2>\n<p>It&#8217;s also possible to iodinate benzene using I<sub>2<\/sub>\u00a0, but the activation step is\u00a0 different. <sub>\u00a0<\/sub>\u00a0Here, however, it turns out that a Lewis acid <strong>catalyst<\/strong> is not sufficient to make iodine an active enough electrophile to react with most aromatic rings.<\/p>\n<p>Instead,\u00a0 a stoichiometric amount of an\u00a0<strong>oxidant<\/strong> is used to convert I<sub>2<\/sub> to I<sup>+\u00a0<\/sup>. A common example cited is HNO<sub>3<\/sub>, which in the presence of additional acid (e.g. H<sub>2<\/sub>SO<sub>4<\/sub>) is a source of the very active oxidant [<strong>NO<sub>2<\/sub><\/strong>]<sup>+<\/sup>\u00a0which converts I<sub>2<\/sub> to I+ .\u00a0 [<a href=\"#notethree\">Note 3<\/a>]<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15912\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-iodination-of-benzene-mechanism-step-1-is-oxidation-to-give-iodonium-ion.gif\" alt=\"iodination of benzene mechanism step 1 is oxidation to give iodonium ion\" width=\"600\" height=\"132\" \/><\/p>\n<p>Once formed, the benzene ring then reacts with I<sup>+\u00a0<\/sup>in the two-step electrophilic aromatic substitution mechanism to give the new <strong>carbon-iodine bond.<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15913\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-electrophilic-aromatic-iodination-mechanism-with-iodonium-ion.gif\" alt=\"electrophilic aromatic iodination mechanism with iodonium ion\" width=\"600\" height=\"420\" \/><\/p>\n<p>The exact identity of &#8220;B&#8221; will depend on the oxidant used to convert I<sub>2<\/sub> into I+ . A single equivalent of water will do the trick, for example.<\/p>\n<h2><strong><a id=\"six\"><\/a>6. Summary: Halogenation of Benzene<\/strong><\/h2>\n<p>In the cases of chlorine, bromine, and iodine, electrophilic aromatic substitution follows three steps.<\/p>\n<ul>\n<li><strong>Activation of the electrophile<\/strong> by a Lewis acid catalyst <span style=\"color: #993366;\"><em>(or stoichiometric oxidant, in the case of iodine)<\/em><\/span><\/li>\n<li><strong>Attack<\/strong> of the activated electrophile by the <strong>aromatic ring.<\/strong><\/li>\n<li><strong>Deprotonation<\/strong> to regenerate the aromatic ring.<\/li>\n<\/ul>\n<p>In the next post we&#8217;ll cover two more important electrophilic aromatic substitution reactions: sulfonation and nitration, and they will also follow this three-step pattern!<\/p>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/04\/18\/electrophilic-aromatic-substitutions-1-halogenation\/\" class=\"\"><span>Electrophilic Aromatic Substitutions (1) \u2013 Halogenation of Benzene<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/07\/11\/electrophilic-aromatic-substitution-introduction\/\" class=\"\"><span>Electrophilic Aromatic Substitution: Introduction<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/11\/09\/electrophilic-aromatic-substitution-the-mechanism\/\" class=\"\"><span>Electrophilic Aromatic Substitution \u2013 The Mechanism<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/04\/30\/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation\/\" class=\"\"><span>Electrophilic Aromatic Substitutions (2) \u2013 Nitration and Sulfonation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/05\/17\/friedel-crafts-alkylation-acylation\/\" class=\"\"><span>EAS Reactions (3) \u2013 Friedel-Crafts Acylation and Friedel-Crafts Alkylation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/electrophilic-aromatic-substitution-practice-problems\/\" class=\"\"><span>Electrophilic Aromatic Substitution Practice Problems (MOC Membership)<\/span><\/a><\/li><\/ul><\/div>\n<p><a id=\"noteone\"><\/a><strong>Note 1<\/strong>. There are a few different ways one could depict this; the drawing above shows the pair of electrons in the Fe-Cl bond acting as the base, which is essentially the same as dissociation of Cl- from FeCl<sub>4<\/sub>(-)\u00a0 \u00a0followed by it acting as a base. One could also draw a lone pair from the Cl of FeCl<sub>4<\/sub> acting as a base, giving H-Cl-FeCl<sub>3<\/sub>, followed by breakage of the Fe-Cl bond to give FeCl<sub>3<\/sub> and HCl.<\/p>\n<p><a id=\"notetwo\"><\/a><strong>Note 2<\/strong>. It&#8217;s not that FeCl<sub>3<\/sub> or AlCl<sub>3<\/sub> aren&#8217;t strong enough to do the job here; the problem is that using Br<sub>2<\/sub> in the presence of FeCl<sub>3<\/sub> will lead to some <strong>scrambling<\/strong> of the halogens, resulting in a small amount of chlorination products. Using the bromide salts eliminates this problem.<\/p>\n<p><a id=\"notethree\"><\/a><strong>Note 3<\/strong>. Many other oxidants have found use in this reaction. Another is copper (II) bromide (CuBr<sub>2<\/sub>).<\/p>\n<hr \/>\n<h2><strong><a id=\"quiz\"><\/a>Quiz Yourself!<\/strong><\/h2>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0521-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0522-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0523-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0524-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1723-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1724-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1725-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1726-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1727-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1722-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n<hr \/>\n<h2><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/h2>\n<p>For more detailed references on the individual halogenation reactions (chlorination, bromination, iodination), consult the sections in the <a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\">reaction guide<\/a>. The references here are highlights.<br \/>\nElectrophilic aromatic fluorination <em>is<\/em> possible, and the last two papers describe that.<\/p>\n<p>Electrophilic aromatic chlorination:<\/p>\n<ol>\n<li><strong> The kinetics of aromatic halogen substitution. Part IV. The 1-halogenonaphthalenes and related compounds<\/strong><br \/>\nP. B. D. de la Mare and P. W. Robertson<strong><br \/>\n<\/strong><em>J. Chem. Soc.,<\/em><strong> 1948, <\/strong>100-106<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/1948\/jr\/jr9480000100#!divAbstract\">10.1039\/JR9480000100<\/a><br \/>\nAn early paper studying the kinetic of electrophilic aromatic halogenation.<\/li>\n<li><strong>Aromatic Substitution. XVII. Ferric Chloride and Aluminum Chloride Catalyzed Chlorination of Benzene, Alkylbenzenes, and Halobenzenes<\/strong><br \/>\nGeorge A. Olah, Stephen J. Kuhn, and Barbara A. Hardie<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1964,<\/strong> <em>86<\/em> (6), 1055-1060<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01060a017\">10.1021\/ja01060a017<\/a><\/li>\n<li><strong>Rates of Chlorination of Benzene, Toluene and the Xylenes. Partial Rate Factors for the Chlorination Reaction<br \/>\n<\/strong>Herbert C. Brown and Leon M. Stock<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1957, <\/strong><em>79<\/em> (19), 5175-5179<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01576a025\">1021\/ja01576a025<\/a>Electrophilic aromatic Bromination:<\/li>\n<li><strong>Relative Rates of Bromination of Benzene and the Methylbenzenes. Partial Rate Factors for the Bromination Reaction<br \/>\n<\/strong>Herbert C. Brown and Leon M. Stock<br \/>\n<em>Journal of the American Chemical Society<\/em><strong> 1957, <\/strong><em>79<\/em> (6), 1421-1425<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01563a040?src=recsys\">1021\/ja01563a040<\/a><\/li>\n<li><strong>Aromatic Substitution. XIV. Ferric Chloride Catalyzed Bromination of Benzene and Alkylbenzenes with Bromine in Nitromethane Solution<\/strong><br \/>\nGeorge A. Olah, Stephen J. Kuhn, Sylvia H. Flood and Barbara A. Hardie<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1964,<\/strong> <em>86<\/em> (6), 1039-1044<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja01060a014\">10.1021\/ja01060a014<\/a><\/li>\n<li><strong>Aromatic Substitution. XV. Ferric Chloride Catalyzed Bromination of Halobenzenes in Nitromethane Solution<br \/>\n<\/strong>George A. Olah, Stephen J. Kuhn, Sylvia H. Flood, and Barbara A. Hardie<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em> <strong>1964,<\/strong> <em>86<\/em> (6), 1044-1046<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01060a015\">1021\/ja01060a015<\/a>Electrophilic aromatic iodination:<\/li>\n<li><strong>Halogenation with copper(II) halides. Synthesis of aryl iodides<\/strong><br \/>\nWilliam C. Baird and John H. Surridge<br \/>\n<em>The Journal of Organic Chemistry<\/em> <strong>1970,<\/strong> <em>35<\/em> (10), 3436-3442<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo00835a055\">10.1021\/jo00835a055<\/a><br \/>\nA simple and straightforward method for synthesizing monoiodoarenes using CuI<sub>2<\/sub> as the iodinating agent.<\/li>\n<li><strong>Electrophilic Fluorination of Aromatics with Selectfluor\u2122 and Trifluoromethanesulfonic Acid<br \/>\n<\/strong>Tatyana Shamma, Herwig Buchholz, G.K. Surya Prakash, and George A. Olah<strong><br \/>\n<\/strong><em>Israel J. Chem<\/em>. <strong>1999<\/strong>, <em>39<\/em> (2), 207-210<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/abs\/10.1002\/ijch.199900026\">1002\/ijch.199900026<\/a><br \/>\nThis paper describes the use of Selectfluor\u2122 as a reagent for electrophilic aromatic fluorination. Selectfluor is a commercially available, easily-handled solid, and a convenient source of \u201cF<sup>+<\/sup>\u201d due to the N-F bond.<\/li>\n<li><strong>Palladium-catalysed electrophilic aromatic C\u2013H fluorination<br \/>\n<\/strong>Kumiko Yamamoto, Jiakun Li, Jeffrey A. O. Garber, Julian D. Rolfes, Gregory B. Boursalian, Jannik C. Borghs, Christophe Genicot, J\u00e9r\u00f4me Jacq, Maurice van Gastel, Frank Neese &amp; Tobias Ritter<strong><br \/>\n<\/strong><em>Nature <\/em><strong>2018, <\/strong><em>554<\/em>, 511\u2013514<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.nature.com\/articles\/nature25749\">10.1038\/nature25749<\/a><strong><br \/>\n<\/strong>This paper is more advanced and covers a current topic in organometallic chemistry \u2013 the use of Pd(IV) fluorides for fluorination. For those following the literature, Prof. Melanie Sanford (U. Michigan) and Prof. Tobias Ritter (this paper, Harvard, now at Max Planck Institute (Germany)) have been going back and forth on this topic.<\/li>\n<\/ol>\n<p>&#8216;,&#8217;Electrophilic Aromatic Substitutions (1) &#8211; Halogenation of Benzene<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Halogenation of Benzene via Electrophilic Aromatic Substitution Unlike alkenes, benzene does not undergo rapid chlorination or bromination with Cl2 or Br2 When it does undergo <\/p>\n","protected":false},"author":1,"featured_media":15904,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1297],"tags":[],"post_folder":[],"class_list":["post-11495","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-aromatic-reactions"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Electrophilic Aromatic Substitutions: Chlorination and Bromination<\/title>\n<meta name=\"description\" content=\"Halogenation of benzene (i.e. chlorination, iodination, and bromination of benzene) via electrophilic aromatic substitution with examples and mechanisms.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.masterorganicchemistry.com\/2018\/04\/18\/electrophilic-aromatic-substitutions-1-halogenation\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Electrophilic Aromatic Substitutions: Chlorination and Bromination\" \/>\n<meta property=\"og:description\" content=\"Halogenation of benzene (i.e. chlorination, iodination, and bromination of benzene) via electrophilic aromatic substitution with examples and mechanisms.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.masterorganicchemistry.com\/2018\/04\/18\/electrophilic-aromatic-substitutions-1-halogenation\/\" \/>\n<meta property=\"og:site_name\" content=\"Master Organic Chemistry\" \/>\n<meta property=\"article:publisher\" content=\"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/\" \/>\n<meta property=\"article:published_time\" content=\"2018-04-18T12:00:35+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2026-04-18T02:18:49+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-halogenation-of-benzene-chlorination-and-bromination-of-benzene-with-lewis-acid-catalysis-fecl3.gif\" \/>\n\t<meta property=\"og:image:width\" content=\"862\" \/>\n\t<meta property=\"og:image:height\" content=\"680\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/gif\" \/>\n<meta name=\"author\" content=\"James Ashenhurst\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"James Ashenhurst\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"13 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/04\\\/18\\\/electrophilic-aromatic-substitutions-1-halogenation\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/04\\\/18\\\/electrophilic-aromatic-substitutions-1-halogenation\\\/\"},\"author\":{\"name\":\"James Ashenhurst\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\"},\"headline\":\"Electrophilic Aromatic Substitutions (1) &#8211; 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