N-bromobutanimide → 1-(Bromomethyl)-4-fluoro-2-iodobenzene

Participants

Reaction Steps

A solution of 23.6 g of 2-iodo-4-fluorotoluene in 50 ml of tetrachloromethane was treated with 0.2 g of dibenzoyl peroxide and 19.6 g of N-bromosuccinimide. The mixture was then refluxed for 6 hours and illuminated by a 200 W bulb. After cooling, the spearated succinimide was filtered off and washed with 15 ml tetrachloromethane. The filtrate was evaporated and the residue distilled. There was obtained 24.8 g of 4-fluoro-2-iodobenzyl bromide with a b.p. of 130°-140° C./20 Torr. The product crystallized on standing and a sample recrystallized from petroleum ether; m.p. 71°-73° C.

Provenance & Evidence