Water → HCID 12531898, compound

Participants

Reaction Steps

To a solution of 2.8 g of p-fluorophenol, 1.19 g of sodium methoxide and 50 mg of potassium iodide in 40 ml of methanol was added 7.43 g of methyl α-bromo-α-[p-(p-chlorophenylthio)phenyl]acetate in 10 ml of benzene. The mixture was refluxed overnight and then cooled to room temperature. The mixture was poured into 100 ml of water and extracted with 2 × 75 ml of ether. The combined extracts were washed with 50 ml of 5% NaOH, 50 ml water, saturated brine, and dried (MgSO4). Evaporation of the solvent at reduced pressure afforded an amber oil, which was chromatographed on 100 g of silica gel (benzene). Concentration of the eluate yielded an amber oil which crystallized on trituration with 100 ml of petroleum ether, mp 84.5°-86.5° C (weight 6.05 g). Recrystallization from 50 ml of hexane yielded 5.3 g of a white solid, mp 84.5°-87° C.

Provenance & Evidence