N-bromobutanimide → Phenyl N-Methoxy-N-(2-bromomethylphenyl)carbamate

Participants

Reaction Steps

A mixture of 324 g (1.3 mol) of phenyl N-methoxy-N-(2-methylphenyl)carbamate (Example 2b), 258 g (1.45 mol) of N-bromosuccinimide and 1 g of azoisobutyronitrile in 1 1 of CCl4 is irradiated using a 300 W UV lamp for about 6 hours, whereby the reaction mixture is heated to boiling. 13 g of N-bromosuccinimide are then added and the mixture is irradiated for a further 8 hours. It is then cooled to room temperature and the precipitated succinimide is filtered off. The organic phase is then extracted with water, dried over MgSO4 and concentrated. The residue crystallizes and is stirred with cyclohexane. 300 g (68%) of the title compound are obtained as a beige solid.

Provenance & Evidence