Methanol → 4-Bromo-2-fluoro-benzoic acid methyl ester

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Reaction Steps

Dissolve 4-bromo-2-fluoro-benzoic acid (15 g, 68.5 mmol) in methanol (70 mL). Add concentrated sulfuric acid (500 μl) to the solution and heat the mixture to reflux for 20 h under a nitrogen atmosphere. Cool the mixture to room temperature and concentrate in vacuo. Dissolve the residue in EtOAc (200 mL) and wash successively with saturated aqueous NaHCO3 (50 mL) and water (2×50 mL). Dry the organic layer over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate (15.4 g, 96%). GC-MS m/z: 232 (M+).

Provenance & Evidence