Synthesis of Acenaphthene-1-carboxylic Acid Using Lithiated Tris(methylthio)methane to Carboxylate 1-Bromoacenaphthene

Article abstract of DOI:10.1055/s-1990-26925

A new synthesis of acenaphthene-1-carboxylic acid (4) in 3 steps and 78 percent overall yield from 1-bromoacenaphthene (1) is described.In the key step, lithiated tris(methylthio)methane is reacted with 1-bromoacenaphthene to give 1-acenaphthene (2).Methanolysis of 2 gives racemic methyl acenaphthene-1-carboxylate 3, which is resolved by chiral chromatography.The usefulness of tris(methylthio)methyllithium as a carboxyl carbanion equivalent is illustrated by the conversion of three other bromides to the corresponding methoxycarbonyl derivatives.