HCID 67439036, compound → HCID 67438076, compound

Participants

Reaction Steps

39.4 g (242 mmol) of iron(III) chloride are initially charged in 200 ml of dichloromethane. At room temperature, a solution of 7.20 g (24.2 mmol) of 5-[2-(benzyloxy)ethyl]-3-(4-fluorophenyl)-1H-pyrazole in 90 ml of dichloromethane is added dropwise. After 20 min, the reaction mixture is washed with 2×100 ml of water. The combined aqueous phases are adjusted to pH 5-6 using sodium bicarbonate and extracted with 2×100 ml of ethyl acetate. The combined organic phases are washed with water, dried over MgSO4 and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel (cyclohexane/ethyl acetate) gives 3.40 g (67%) of the desired product; log P(HCOOH): 1.39; 1H-NMR (DMSO-d6): 7.79 (dd, 2H), 7.19 (dd, 2H), 6.47 (s, 1H), 4.79 (t, 1H), 3.65 (m, 2H), 2.76 (t,

Provenance & Evidence