Synthesis 2009(11): 1807-1810  
DOI: 10.1055/s-0029-1216793
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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: [email protected];
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Publikationsverlauf

Received 9 January 2009
Publikationsdatum:
30. April 2009 (online)

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.

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