Sodium hydride → (3-Amino-4-fluorophenoxy)acetic acid methyl ester

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Reaction Steps

3-Amino-4-fluorophenol (3.0 g) was added to a stirred suspension of sodium hydride (60% in oil, 0.94 g) in N,N-dimethylformamide (30 mL) at 0° C., and the resulting mixture was warmed to room temperature for 15 minutes. The mixture was cooled to 0° C. treated with bromoacetic acid methyl ester (3.3 g), and then stirred at room temperature for 2 hours. The mixture was treated with dilute aqueous ammonium chloride solution and extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of toluene, dichloromethane and ethyl acetate (2:1:0, 0:1:0 to 0:20:1 by volume) gave title compound (2.7 g).

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