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Synthesis 2010(6): 911-913  
DOI: 10.1055/s-0029-1218631
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Improved Synthesis of the Benzyne Precursor 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate

Darcy J. Atkinson, Jonathan Sperry, Margaret A. Brimble*
Department of Chemistry, University of Auckland, 23 Symonds Street, Auckland, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;
Further Information

Publication History

Received 12 November 2009
Publication Date:
04 January 2010 (online)

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Abstract

An alternate procedure for the preparation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, a coveted benzyne precursor, is described. Modifications to existing methods result in a dramatic reduction in the overall reaction time and eliminate the use of organolithium reagents. This new procedure proceeds in four steps in 81% overall yield from 2-chlorophenol.

Key words

benzyne - aryne - precursor

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4

Compound 1 costs more than NZ$ 210 for 5 g (Sigma-Aldrich).

11

Very recently, Bronner and Garg reported an ortho-metallation based preparation of 1 from phenol in 3 steps and 66% overall yield: Bronner, S. M.; Garg, N. K.; J. Org. Chem.; in press; DOI: 10.1021/jo90201.