A Facile Synthesis of 4-(Trialkylmethyl)anilines by the Reaction of 4-(Trifluoromethyl)aniline with Grignard Reagents

Abstract

The treatment of 4-(trifluoromethyl)aniline (7) with primary Grignard reagents in ether yields the title products 14 (50–75%). A mechanistic pathway involves a series of fluoride elimination reactions followed by addition of the Grignard reagent to the resultant nonaromatic intermediate after each elimination step.