Benzylic bromination of a methyl-anthraquinone

SyntheticPage 454
Published Aug 03, 2010


Reaction Scheme

Procedure

A mixture of 1,2,4-trimethoxy-3-methyl-anthraquinone (3.029 g, 9.7 mmol), N-bromosuccinimide (1.8 g, 10.1 mmol) and dibenzoyl peroxide (84 mg) was refluxed for 10 h in CCl4 (200 cm3).   The suspension was filtered with charcoal and Celite through flash silica gel (10 g), washing with CCl4 (2 x 30 cm3). Evaporation gave a yellow solid (3.53 g, 93% yield).

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