Benzoyl Peroxide → 1,3-Dibromo-2-(bromomethyl)-5-methoxybenzene

Participants

Reaction Steps

To a suspension of 5.0 g of 2,6-dibromo-4-methoxytoluene in 90 mL of CCl4 was added N-bromosuccinimide and benzoyl peroxide. The resulting mixture was heated to reflux and stirred at the refluxing temperature while irradiating with a sunlamp for 2 h, then cooled and concentrated. The resulting residue was dissolved in 1:1 hexanes-Et2O and filtered through a pad of silica gel, then purified by flash chromatography on a Biotage 40M column, eluting with 98:2 hexanes-Et2O, to yield 2,6-Dibromo-4-methoxy-benzyl bromide as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 7.11 (s, 2H); 4.82 (s, 2H); 3.80 (s, 3H).

Provenance & Evidence