A rapid and practical synthesis of gem-dibromoalkanes has been developed. A variety of alkyl and aromatic aldehydes are converted into their corresponding gem-dibromoalkanes within 10 minutes by using tribromide reagent. The protocol is also appliable to the bromination of alcohols, accessing alkyl bromides with inversion of configuration.

Abstract

gem-Dibromoalkanes are important synthetic building block in organic chemistry, but their preparation is still troublesome. Herein, we have developed a simple and practical protocol for the synthesis of gem-dibromoalkanes from aldehydes using tetrabutylammonium tribromide and triphenyl phosphite. A variety of alkyl and aromatic aldehydes can be transformed into the corresponding products within 10 minutes. This protocol is also applicable to alcohols, and the configuration of chiral alcohol is inverted during the process with excellent enantiopurity.