N-bromobutanimide → 1-(Bromomethyl)-3-methoxy-5-methylbenzene

Participants

Reaction Steps

A refluxing solution of 3,5-dimethylanisole (13 g), azoisobutyronitrile (1.6 g) and N-bromosuccinimide (17 g) in carbon tetrachloride (100 ml) was irradiated with light for 6 h. The solution was filtered and the solvent removed in vacuo. The residue was purified by chromatography on silica gel (eluting with 0-5% ethyl acetate--petroleum ether bp=60°-80° C.) to yield 3-bromomethyl-5-methylanisole.

Provenance & Evidence