Dichloromethane → HCID 17985031, compound

Participants

Reaction Steps

3.1 g (6.4 mmol) of (rac) 1,1,1,-trifluoro-4-(4-chloro-2-methoxyphenyl)-2-[(8-fluoro-2-methyl-quinazol-5-yl)iminomethyl]-4-methyl-pentan-2-ol is introduced into 50 ml of dichloromethane and 128 ml of a 1 M solution of boron tribromide in dichloromethane is added in drops at −75° C. It is allowed to reach −20° C. within 2.5 hours. Then, the reaction mixture is added to 300 ml of a saturated NaHCO3 solution, stirred for 15 more minutes, the phases are separated, the aqueous phase is extracted with dichloromethane, the combined organic phases are washed with saturated NaHCO3 solution and saturated NaCl solution and dried with sodium sulfate. After the solvent is removed in a rotary evaporator, the crude product is chromatographed on silica gel (eluant: hexane/ethyl acetate 3:1 to 1:1). Then, it is purified again by means of HPLC. 650 mg (26%) of the desired product is obtained as a yellow solid.

Provenance & Evidence