Iodoethane → (3-Cyano-4-fluoro-phenyl)-acetic acid ethyl ester

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To a suspension of (3-cyano-4-fluoro-phenyl)-acetic acid (500 mg, 2.79 mmol) (Preparation 126) and potassium carbonate (770 mg, 5.58 mmol) in DMF (5 mL) was added ethyl iodide (0.89 mL, 11.16 mmol) and the reaction mixture stirred at room temperature for 4 hours. The crude reaction mixture was poured onto water (10 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with water (5×10 mL), brine (10 mL), dried over sodium sulphate, filtered and concentrated under reduced pressure to afford the title compound as an off-white solid in 87% yield, 500 mg.

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