Ritter reaction of 1-aryl-1-fluoro-2-haloethanes

Abstract

Fluorinated phenethyl bromides 1, 2, and 3, prove to be totally inert under Ritter reaction conditions in the presence of either SnCl4 or AgNO3, due to the strong deactivation by the gem-difluoro unit. Subjecting 2-bromo-1-fluoro-1-phenylethane to SnCl4 in MeCN at elevated temperatures led to formation of 2-methyl-4-phenyl-4,5-dihydrooxazole.