Dimethylcyanamide → 5-Bromophthalide

Participants

Reaction Steps

A solution of 0.43 g (2.0 mmol) of 4-bromo-2-methyl-benzoic acid, 0.34 g (1.9 mmol) of N-bromosuccinimide and 20 mg of azaisobutyronitrile in 7 ml of methyl propionate is heated to boiling for 1 hour under a nitrogen atmosphere and irradiated with a mercury vapour lamp. The reaction mixture is concentrated, taken up in methylene chloride, washed with H2O, dried with Na2SO4 and purified by flash chromatography (silica gel; ethyl acetate/petroleum ether=5:95 to 15:85).

Provenance & Evidence