Dimethyl Sulfide → HCID 22031902, compound

Participants

Reaction Steps

2.2 mL n-butyl lithium (2.66 M hexane solution) was added dropwise to a solution of 1.85 g benzhydrylidene-(5-bromo-2-fluorophenyl)-amine (compound in Production Example 336) in 10 mL tetrahydrofuran at −70° C., then the mixture was stirred for 15 minutes, a solution of 0.53 mL methyl sulfide in 5 mL tetrahydrofuran was added dropwise thereto, and the mixture was stirred at 0° C. for 2 hours. An aqueous saturated ammonium chloride solution was added thereto, and the reaction mixture was diluted with water, extracted with ethyl acetate and washed with brine. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane) to give 1.24 g of the title compound (colorless oil).

Provenance & Evidence