Hydrochloric Acid → HCID 43554866, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-fluorobenzaldehyde (2.50 g, 20.1 mmol) in N,N-dimethylformamide (13 mL) were added potassium carbonate (3.33 g, 24.1 mmol) and 3,4-difluorophenol (2.61 g, 20.1 mmol) in turn, and the mixture was stirred for 2.5 hours at 135° C. Water was added to the reaction mixture, which was extracted with ethyl acetate. Then the ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the residue were added ethanol (50 mL) and sodium borohydride (760 mg, 20.1 mmol) in turn, and the mixture was stirred for 4 hours at room temperature. Water was added to the reaction mixture, which was brought to pH 4 with 3 mol/L hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→3:1) to afford 4.40 g of pale yellow liquid title compound. Yield 93%.

Provenance & Evidence