Organic reactions in melts and solids. Part IV. Hydrogenolysis of bromo-compounds by neat benzoin

Abstract

Bromine was substituted by hydrogen when certain bromo-compounds were melted together with neat benzoin. The reaction is highly selective. Benzoin (but not other secondary alcohols) serves as a hydrogenating agent and only bromine adjacent to an activating function (e.g., a keto or ester group) is substituted. Hydrogen bromide is a specific catalyst for the reaction. The reaction is fast, gives high yields, and is of preparative value.