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Chloromethylation of nitroaromatics

23 September 2019

A novel synthetic method of chloromethylation of nitroaromatics employing vicarious nucleophilic substitution was developed and optimized in Petr Beier Group. 

In a paper published in Organic Letters, the IOCB Prague researchers Viktor Khutoriansky, Blanka Klepetářová, and Petr Beier found the conditions for this reaction exhibiting good yields, high regio- and chemoselectivity and wide functional group tolerance. Under cryogenic conditions, the reactive agent allowing for this kind of transformation is the dichloromethane lithium salt. 

Sensitivity of the resulting intermediate towards aerial oxygen can also be utilized in a slightly changed protocol to make this method a convenient way of formylating nitroaromatics yielding some nitrobenzaldehydes that are otherwise difficult to obtain.

If you want to read more about this method, widening the possibilities of traditional organic synthesis, head to the paper: Viktor V. Khutorianskyi, Blanka Klepetářová, and Petr Beier. Organic Letters 2019 21 (14), 5443-5446. doi.org/10.1021/acs.orglett.9b01676 
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