Benzylic Brominations with N-Bromosuccinimide in (Trifluoromethyl)benzene

Diana Suarez; Gilles Laval; Shang-Min Tu; Dong Jiang; Claire L. Robinson; Richard Scott; Bernard T. Golding

doi:10.1055/s-0029-1216793

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Synthesis 2009(11): 1807-1810
DOI: 10.1055/s-0029-1216793

PAPER

Benzylic Brominations with N-Bromosuccinimide in (Trifluoromethyl)benzene

Diana Suarez, Gilles Laval, Shang-Min Tu, Dong Jiang, Claire L. Robinson, Richard Scott, Bernard T. Golding*
School of Chemistry, Bedson Building, University of Newcastle upon Tyne, Newcastle upon Tyne, NE1 7RU, UK
Fax: +44(191)2226929; e-Mail: b.t.golding@ncl.ac.uk;

Further Information

Publication History

Received 9 January 2009
Publication Date:
30 April 2009 (online)

Abstract
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Abstract

A variety of benzylic brominations were performed by using N-bromosuccinimide in (trifluoromethyl)benzene with photochemical activation in the presence of 2,2′-azobisisobutyronitrile, 1,1′-azobis(cyclohexanecarbonitrile), or benzoyl peroxide as the radical initiator. This system provides clean, rapid, and high-yielding reactions with replacement of conventional solvents, such as tetrachloromethane, by less-toxic (trifluoromethyl)benzene.

Key words

benzylic bromination - (trifluoromethyl)benzene - free radical - N-bromosuccinimide - azobisisobutyronitrile

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