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

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A solution of methyl 4-bromo-3-(bromomethyl)benzoate (37.5 g, 122 mmol) in MeOH (1.1 L) 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% aqueous solution of NaHCO3 (200 mL) and brine (200 mL), dried (MgSO4) and concentrated affording the title compound as a beige solid (29.8 g, 94%). HPLC (Method A), Rt 4.4 min (purity: 93.0%). UPLC/MS, M−(ESI): 227.2. 1H NMR (DMSO-d6, 300 MHz) δ 8.06 (m, 1H), 7.83 (m, 2H), 4.54 (m, 2H), 3.90 (s, 3H), 3.45 (s, 3H).

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