Dehydrobromination of 1,2-Dibromoethoxyethane Using Various Amine Bases

Article abstract of DOI:10.1021/jo00369a004

1,2-Dibromoethoxyethane was treated with a number of basic reagents, mainly tertiary amines, to accomplish dehydrobromination to 1-bromo-2-ethoxyethene, a precursor to an acetaldehyde carbanion equivalent.The yield of this vinyl bromide and the other common byproducts of reaction varied markedly depending on the base and reaction conditions employed.Direct distillation of the product under reduced pressure from a tertiary amine solution was the method of choice, showing little if any effect of temperature and giving reproducible results.Following this procedure, N,N-dimethyldodecylamine was the preffered base for this reaction.This paper presents results of the dehydrobromination reaction using more than 30 different bases and conditions