Water → Methyl 2-(bromomethyl)-4-methoxybenzoate

Participants

Reaction Steps

To a solution of methyl 4-methoxy-2-methylbenzoate (1 g, 5.6 mmol) in CCl4 (25 mL) was added dropwise N-bromosuccinimide (1.1 g, 6.2 mmol) previously dissolved in CCl4 (5 mL) and a catalytic amount of benzoyl peroxide. The mixture was refluxed for 2 hours, cooled to room temperature and poured onto iced water. The aqueous mixture was extracted with DCM (3×), and the combined organics were dried over MgSO4, filtered, and concentrated in vacuo to provide 2.1 g of the titled product as light yellow solid (˜100% yield): [M+H+] m/z 260.

Provenance & Evidence