Water → Ethyl 2-(4-fluoroanilino)acetate

Participants

Reaction Conditions

Reaction Steps

Ethyl bromoacetate (8.09 g, 48.4 mmol) was slowly added to a solution of 4-fluoroaniline (5.38 g, 48.4 mmol) and sodium acetate (5.16 g, 62.9 mmol) in ethanol (62 mL) and the mixture was heated at 80° C. for 2 h. Water was added and the reaction was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-20% EtOAc in hexanes) to afford ethyl 2-((4-fluorophenyl)amino)acetate (1).

Provenance & Evidence