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Synthesis 1990; 1990(6): 517-519
DOI: 10.1055/s-1990-26925
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Synthesis of Acenaphthene-1-carboxylic Acid Using Lithiated Tris(methylthio)methane to Carboxylate 1-Bromoacenaphthene

Paul R. Halfpenny* , David C. Horwell, David C. Rees
  • *Parke Davis Research Unit, Addenbrookes Hospital site, Hills Road, Cambridge, CB2 2QB, England
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Publication Date:
17 September 2002 (online)

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A new synthesis of acenaphthene-1-carboxylic acid (4) in 3 steps and 78% overall yield from 1-bromoacenaphthene (1) is described. In the key step, lithiated tris(methylthio)methane is reacted with 1-bromoacenaphthene to give 1-[tris(methylthio)methyl]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.