4-Methoxyphenol → 2,6-Dibromo-4-methoxyphenol

Participants

Reaction Steps

To 4-methoxyphenol (10.00 g, 80.6 mmol) in CH2Cl2 (70 mL), add a stirred solution of benzyltrimethylammonium tribromide (69.10 g, 177.2 mmol) in CH2Cl2 (500 mL) and MeOH (200 mL). Stir the reaction for 12 hours and remove the solvent in vacuo. Add methyl tert-butyl ether (MTBE) (600 mL) and collect the precipitate (benzyltrimethylammonium bromide) by filtration and wash with MTBE (200 mL). Filter the organics through Celite® and concentrate to provide the subtitled product (23.0 g, >95%) as an orange solid that may be used without purification. 1H NMR (DMSO-d6) δ 3.69 (s, 3H), 7.14 (s, 2H), 9.32 (s, 1H).

Provenance & Evidence