Carbon tetrabromide → 2-[5-Bromo-1-[(4-chlorophenyl)sulfonyl]-2-methylpentyl]-1,4-difluorobenzene

Participants

Reaction Steps

The 5-[(4-chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-4-methyl-1-pentanol (290 mg, 0.746 mmol) obtained in Example 39 and carbon tetrabromide (290 mg, 0.874 mmol) were dissolved in methylene chloride (8 ml). While stirring under ice cooling, a solution obtained by dissolving triphenylphosphine (230 mg, 0.877 mmol) in methylene chloride (2 ml) was added dropwise to the resulting solution. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 3 days. To the reaction mixture were added carbon tetrabromide (290 mg, 0.874 mmol) and triphenylphosphine (230 mg, 0.877 mmol) under ice cooling, followed by stirring at room temperature for 6 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=15:1), whereby the title compound (331 mg, 98%) was obtained as a colorless oil.

Provenance & Evidence