Methanol → Methyl 4-bromo-3-(methoxymethyl)benzoate

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Reaction Steps

A solution of methyl 4-bromo-3-(bromomethyl)benzoate obtained in step 1 (37.50 g; 121.77 mmol) in MeOH (1 125 mL) was refluxed for 4 days. After concentration, the mixture was partitioned between EtOAc (500 mL) and water (200 mL). The organic layer was washed with a 5% NaHCO3 aqueous solution (200 mL), brine (200 mL), dried over MgSO4 and concentrated affording the title compound as a beige solid (29.8 g, 94%). 1H NMR (DMSO-d6) δ 8.06-8.05 (m, 1H), 7.83 (d, J=1.23 Hz, 2H), 4.54 (m, 2H), 3.90 (s, 3H), 3.45 (s, 3H). LC/MS (Method B): 227.2 (M−H)−. HPLC (Method A) Rt 4.42 min (Purity: 93.0%).

Provenance & Evidence