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Paper | Regular issue | Vol 31, No. 7, 1990, pp.1261-1270
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5343
The Selective Benzylic Bromination of o-Xylenes. A Useful Synthesis of Phthalides

Vernon G. S. Box* and George P. Yiannikouros

*Department of Chemistry, The City College of the City University of New York, Convent Avenue @ 138th Street, New York, NY 10031, U.S.A.

Abstract

The free radical bromination of aryl methyl groups can be controlled by the strategic positioning of a remote stereo-electroni blocking group on the aryl ring. This tactic leads to the efficient synthesis of selectively benzylically brominated molecules whichare useful synthetic intermediates. This methodology has been applied to the synthesis of some phthalides.