Efficient, practical and reproducible reactions of a commercial hydrochlorofluorocarbon

Abstract

We report a reliable and reproducible procedure for the conversion of readily-available hydrochlorofluorocarbon 1-chloro-2,2,2-trifluoroethane (HCFC-133a) to a metallated difluoroalkene (1-chloro-1-lithio-2,2-difluoroethene) which can be trapped with a range of electrophiles to afford high isolated yields of products. 1-Chloro-1-lithio-2,2-difluoroethene generated by our method reacts efficiently with aldehydes and ketones, Group (IV) halides, an epoxide and a sulfur electrophile. Less reactive, softer electrophiles fail to trap the reactive intermediate.