Chloroacetic Acid → 2-[2-(3-Fluorophenyl)ethoxy]acetic acid

Participants

Reaction Steps

To a solution of 2-(3-fluoro-phenyl)-ethanol (4.0 g, 28.5 mmol) in DMF (60 ml) was added sodium hydride (60% dispersion in oil, 2.40 g, 60 mmol). The suspension was heated to 60° C. for 0.75 hours before chloroacetic acid (4.72 g, 50 mmol) was added dropwise. After 36 hours at 60° C. the brown reaction mixture was brought to dryness under reduced pressure, dissolved in EtOAc and washed with 1M HCl, water and brine. The organic layers were dried (MgSO4), filtered, the solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, EtOAc/heptane 3:1) to yield the title compound (2.02 g, 18 mmol; 36%) as colorless liquid. MS: m/e=197.4 [M−H]−.

Provenance & Evidence