Methanol → Methyl 3-bromo-2,6-dimethoxybenzoate

Participants

Reaction Steps

3-Bromo-2,6-dimethoxybenzoic acid (5.0 g, 19.2 mmol) and thionyl chloride (10 ml) were heated to reflux for 2 h. The mixture was then concentrated in vacuo and diluted with CH2Cl2 (20 ml) and added to a solution of MeOH (614 mg, 38.4 mmol) and triethylamine (3.88 g, 38.4 mmol) in CH2Cl2 (100 ml) at 0° C. The resulting mixture was allowed to warm to RT and stirred for 64 h. The organics were washed with 10% HCl (50 ml), brine (50 ml) and dried (MgSO4) and purified by chromatography (0–50% EtOAC in heptane) to leave a white solid (4.17 g).

Provenance & Evidence