Synthesis 2009(11): 1807-1810  
DOI: 10.1055/s-0029-1216793
© 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:;
Further Information

Publication History

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


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.


Radleys Carousel from Radleys Discovery Technologies; Shire Hill, Saffron Walden, Essex, CB11 3AZ, UK