Methanol → Benzoic acid, 4-bromo-3,5-dihydroxy-, methyl ester

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Reaction Steps

To a solution of 4-bromo-3,5-dihydroxybenzoic acid (13.89 g, 59.6 mmol) in methanol (50 mL) was added H2SO4 (concentrated, 1 mL). The reaction mixture was heated to reflux overnight. The mixture was quenched with H2O (500 mL) and extracted with 10% MeOH in CH2Cl2 (5×500 mL), dried over MgSO4 and concentrated in vacuo to give a white solid (14.8 g, 100% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.47 (s, 2 H) 7.00 (s, 2 H) 3.80 (s, 3 H); LCMS for C8H7BrO4 m/z 249.10 (M+H)+.

Provenance & Evidence