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29.3.2.2.8 Method 8: Chloromethylation of Aromatic Compounds

DOI: 10.1055/sos-SD-029-00127

Benneche, T.Science of Synthesis, (200729151.

Chloromethylation of aromatic compounds is an important synthetic reaction that has been well covered in the literature.[‌178‌] When chloromethyl methyl ether is used as the alkylating agent, the reaction can be performed without a catalyst[‌179‌] or with a Brønsted acid[‌180‌,‌181‌] or a Lewis acid catalyst,[‌182‌‌187‌] depending on the substrate. Usually, a weak Lewis acid, such as tin(IV) chloride[‌185‌,‌186‌] or titanium(IV) chloride,[‌183‌,‌187‌] is used to avoid the formation of a diarylmethane, which may be a problem under more strongly acidic conditions.[‌178‌] Treatment of 1-iodo-3-methoxybenzene with chloromethyl methyl ether at room temperature for 3 days gives the bischloromethylated product 137 in 68% yield (Scheme 67).[‌187‌]

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