N-bromobutanimide → 5-(bromomethyl)-2,2-difluorobenzo[d][1,3]dioxole

Participants

Reaction Steps

A mixture of 2,2-difluoro-5-methyl-1,3-benzodioxole (29.0 g, 0.169 mole), N-bromosuccinimide (30.1 g, 0.169 mole), benzoyl peroxide (0.5 g) and carbon tetrachloride (50 ml) is refluxed for 2.5 hours. Carbon tetrachloride (50 ml) is then added to the hot reaction mixture and the solids are filtered off. The filtrate and washings are evaporated to yield 41.0 g of title product, a brown oil; nmr (CCl4) δ 4.38 (S, 2H), 6.8-7.4 (m, 3H). The product is used without further purification in the next step.

Provenance & Evidence