668-45-1

124-41-4

6575-10-6

To a 100 mL solution of 2-chloro-6-fluorobenzonitrile (1.55 g, 10.0 mmol) in anhydrous methanol was added sodium methanolate (4.32 g, 80 mmol). The reaction mixture was heated at 85 °C and stirred overnight. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure. The residue was diluted with 400 mL of dichloromethane (DCM) and washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) and aqueous ammonium chloride (NH4Cl, 2 x 20 mL). The organic phase was dried over anhydrous sodium sulfate (Na2SO4) and concentrated in vacuum. The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 10:1) to afford 2-chloro-6-methoxycyanobenzene (1.5 g, 89.8% yield) as a light yellow solid. LC-MS showed [MH]+ = 168.0.