3,5-Bis(trifluoromethyl)benzyl bromide → HCID 22353131, compound

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask fitted with a reflux condenser and a thermometer 2.76 g (6.6 mmoles) of thioacetate 83 and 250 ml of degassed methyl alcohol are introduced. The mixture is cooled to 0° C. and 356 mg (6.6 mmoles) of sodium methylate are added. The mixture is stirred under argon for one hour at 0° C., and 1.9 g (7.26 mmoles) of 3,5-bis-trifluoromethyl-benzyl bromide are added. The mixture is stirred for 48 hours, volatile substances are removed under reduced pressure, and 100 ml of water are added. The aqueous phase is extracted three times with methylene chloride, the combined organic phases are washed with brine and dried over magnesium sulfate. Volatile substances are removed under reduced pressure, affording 4.54 g of crude 1-[2-(3,5-bis-trifluoromethyl-benzylsulfanyl)-1-phenyl-ethyl]-4-(toluene-4-sulfonyl)-piperazine (compound 84) as a colorless oil. This oil was purified by chromatography on silica gel (eluent: methylene chloride-hexane 65/35 (v/v)), affording 3.26 g of compound 84 as a colorless oil. Yield: 82%.

Provenance & Evidence