Benzoyl Peroxide → 4-(Bromomethyl)-1-chloro-2-methoxybenzene

Participants

Reaction Steps

To a solution of 4-chloro-3-methoxytoluene (200 mg, 1.28 mmol) in carbon tetrachloride (12 mL) was added N-bromosuccinimide (228 mg, 1.28 mmol) and benzoyl peroxide (31 mg, 0.128 mmol). The mixture was heated at reflux for 2 hours. The reaction mixture was allowed to cool to room temperature and the solvent removed in vacuo. The resulting residue was partitioned between DCM and water. The organic layer was separated, dried over sodium sulphate and evaporated to yield an orange oil. The oil was purified by silica gel chromatography eluting with 30% heptanes in DCM to afford the title compound (45 mg) as a 3.5:1:1 mixture with 4-chloro-3-methoxytoluene and 1-chloro-4-(dibromomethyl)-2-methoxybenzene respectively, which was used in the next step without further purification.

Provenance & Evidence