An Efficient and Practical Synthesis of Aryl and Hetaryl α-Keto Esters

Abstract

A general and highly efficient method was developed for the synthesis of α-keto esters by oxidative esterification of 2,2-dibromo-1-(het)arylethanones by sequential treatment with dimethyl sulfoxide and an alkanol. The versatility of the reaction was established by synthesizing a range of α-keto esters by treatment of 2,2-dibromoethanones, derived from aryl or hetaryl ketones, with di­methyl sulfoxide and a cyclic or acyclic primary or secondary alcohol. The mechanism of the reaction was established by means of a detailed study.