4-Fluorophenol → HCID 22612275, compound

Participants

Reaction Conditions

Reaction Steps

To the sodium hydride obtained by washing 351 mg (7.73 mmol) of 50% sodium hydride dispersion in mineral oil with pentane was added 10 mL of dimethylformamide followed by 867 mg (7.73 mmol) of p-fluorophenol. After the hydrogen evolution ceased, 886 mg (3.87 mmol) 1-(2-Fluoro-pyridin-3-yl)-3-phenyl-propan-1-one was added dissolved in a minimum amount of DMF. The mixture was heated to 80° C. for 3 h, and the solvent was evaporated under high vacuum. The residue was partitioned between 200 mL of ether and 50 mL of aqueous 1 N sodium hydroxide solution, and the separated organic layer was washed with aqueous 1 N sodium hydroxide solution (1×50 mL), brine (1×100 mL), dried (Na2SO4), and evaporated to 1.16 g of a white solid. Recrystallization from hexane gave 1.06 g (85% yield) of the title compound as a white solid, mp 82-83° C. Anal. Calcd for C20H16FNO2: C, 74.75; H, 5.02; N, 4.36. Found: C, 74.63; H, 4.97; N, 4.31.

Provenance & Evidence