N-bromobutanimide → 2-Bromo-5-methoxybenzyl bromide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-5-methoxytoluene (20 g, 0.10 mol), N-bromosuccinimide (19.6 g, 0.11 mol), benzoyl peroxide (1 g, 4 mmol), and methylene chloride (200 mL) was irradiated for 18 hr with a flood lamp to effect gentle reflux. The mixture was then cooled to −10° C. for several hours and the solution was decanted away from the precipitated succinimide. The solution was concentrated and the residue was crystallized from chloroform/hexane to give the title compound (19.7 g, 70%) as pale yellow prisms: 1H NMR (CDCl3) δ 7.45 (d, J=8.9 Hz, 1 H, 6.99 (d, J=3 Hz, 1 H, 6.74 (dd, J=8.9, 3 Hz, 1 H), 4.55 (s, 2 H) 3.80 (s, 3 H).

Provenance & Evidence