Benzoyl Peroxide → Methyl 2-(bromomethyl)-3-nitrobenzoate

Participants

Reaction Steps

To a suspension of 100 g of 2-methyl-3-nitrobenzoic acid, methyl ester and 100 g of N-bromosuccinimide in 1000 ml carbon tetrachloride was added 3 g of benzoyl peroxide and the mixture was stirred at reflux temperature for about 24 hours. Additional benzoyl peroxide was then added and refluxing was resumed for another 24 hours. The reaction mixture was cooled, filtered, and the filtrate concentrated in vacuo to afford an oil which crystallized upon cooling. This crude product was dissolved in diethyl ether and the organic layer was washed with saturated aqueous sodium sulfite (one 500-ml portion), water (two 500-ml portions), 2.5% aqueous sodium hydroxide solution (one 500-ml portion), water and brine. Drying and evaporation of the organic layer in vacuo gave a yellow oil which crystallized on standing. Recrystallization from 350 ml n-butyl chloride/cyclohexane (2:1) gave 74 g of 2-(bromomethyl)-3-nitrobenzoic acid, methyl ester, m.p. 67°-70°.

Provenance & Evidence