An Efficient Preparation of Alkyl α-Bromomethylacrylates by Dehydrobromination of Alkyl β,β′-Dibromoisobutyrates with Potassium Fluoride

Abstract

1° and 2° alkyl esters of β,β′-dibromoisobutyric acid are efficiently dehydrobrominated to alkyl α-bromomethylacrylates by anhydrous potassium fluoride (2.5 equiv) in refluxing acetonitrile/DMF (85:15). 3° isobutyrates give reduced yields of acrylates due to accompanying cleavage of the ester by the HF produced.