Ethanol → (4-Fluoro-phenylsulfanyl)-acetic acid methyl ester

Participants

Reaction Steps

A solution of 4-fluorothiophenol (10 g, 78 mmol) in ethanol(200 mL) was treated with powdered KOH (9.6 g), stirred for 30 min at rt, then treated with a solution of bromoacetic acid (10.84 g, 78 mmol) in ethanol (50 mL) and stirred at 80 C for 4 h. the reaction was cooled to rt, partitioned between 1N HCl and EtOAc and the organics were washed with water, dried (Na2SO4), filtered and concentrated. The crude product was dissolved in MeoH (250 mL), cooled to 0 C, treated with SOCl2 (8.5 mL) and stirred at rt overnight. The reaction was quenced with water, concentrated then partitioned between EtOAc (3 times) and water. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated to give 14.6 g of the title compound.

Provenance & Evidence