3-Methoxyphenol → 2-Bromo-5-methoxyphenol

Participants

Reaction Steps

To a solution of 3-methoxy-phenol (1 g, 8.055 mmol) in tetrahydrofuran (30 mL) at room temperature was added N-bromosuccinimide (1.478 g, 8.055 mmol) in several portions. The yellow reaction mixture was stirred at room temperature for 12 h. Sodium bicarbonate solution (5 mL) was added and the product was extracted with diethyl ether (2×100 mL). The organic layers were washed with brine (1×20 mL) and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 10-30% ethyl acetate in hexanes yielded 2-bromo-5-methoxy-phenol (0.801 g, 49%) and 4-bromo-5-methoxy-phenol (0.396 g, 24%).

Provenance & Evidence