Dihalomethylation of Nitroarenes via Vicarious Nucleophilic Substitution of Hydrogen with Trihalomethyl Carbanions

Article abstract of DOI:10.1021/jo00282a025

Trichloro- and tribromomethyl carbanions generated by deprotonation of haloforms with potassium tert-butoxide in a THF-DMF mixture at ca. -70 deg C react with a variety of carbocyclic and heterocyclic nitroarenes according to the vicarious nucleophilic substitution scheme.The reaction provides an efficient and convenient way for the direct introduction of dihalomethyl substituents ortho and para to the nitro group, which in turn can be hydrolyzed to produce nitroaryl aldehydes.