A Regiospecific Construction of α-Haloketones by the Reaction of Enol Borinates with N-Bromo- and N-Chlorosuccinimide. A Convenient Method for Converting Olefins into α-Haloketones and Esters

Abstract

α-Bromo- and α-chloroketones may be synthesized in a regiospecific manner in high yields by treatment of an enol borinate with N-bromo- or N-chlorosuccinimide. This method preassembles the carbon skeleton of the ketone, and thereby avoids the problems (isomer formation, polyhalogenation) inherent in other methods. α-Haloesters are also easily synthesized by this procedure.