Sodium Hydroxide → HCID 67459044, compound

Participants

Reaction Steps

In a nitrogen stream, a solution of 1-benzyloxy-2-[4-(2,2-Difluorovinyl)benzyl]benzene (984.5 mg, 2.93 mmol) in methylene chloride (12 mL) was cooled to −78° C., and a boron tribromide-dimethylsulfide methylene chloride solution (1.0 M, 7.32 mL) was added dropwise thereto. The reaction mixture was stirred at the same temperature for two minutes and under cooling with ice for two hours, and furthermore the boron trifluoride-dimethylsulfide methylene chloride solution (4.39 mL) was added dropwise thereto. The reaction mixture was stirred at the same temperature for 3.5 hours, then a sodium hydroxide aqueous solution and a saturated sodium hydrogencarbonate aqueous solution was added thereto and the mixture was extracted with methylene chloride, and the organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue obtained by distilling the solvent under reduced pressure was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:7)] to obtain the title compound (647.5 mg, 90%).

Provenance & Evidence