4-Fluoro-2-methoxybenzoic acid methyl ester

67-56-1

395-82-4

204707-42-6

General procedure for the synthesis of methyl 4-fluoro-2-methoxybenzoate from methanol and 4-fluoro-2-methoxybenzoic acid: 4-fluoro-2-methoxybenzoic acid (1.7 g, 10 mmol) was dissolved in methanol (100 mL) at 0 °C and thionyl chloride (5.73 g, 48 mmol) was added slowly. The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the solvent was removed by rotary evaporator under vacuum. Saturated aqueous sodium bicarbonate (50 mL) was added to the residue to neutralize the unreacted thionyl chloride, followed by extraction with ethyl acetate (100 mL x 3). The organic phases were combined and dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under vacuum to afford the target product methyl 4-fluoro-2-methoxybenzoate (1.3 g, 70% yield).