Sodium Iodide → (S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol

Participants

Reaction Steps

To a suspension of (S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-((R)-toluene-4-sulfinylmethyl)pentan-2-ol (31.9 g, 76.6 mmol) and sodium iodide (34.4 g, 230 mmol) in 450 mL of anhydrous acetone at −40° C. was added a solution of trifluoroacetic acid anhydride (54.1 mL, 383 mmol) in 200 mL of anhydrous acetone via an addition funnel dropwise over 30 minutes. A greenish brown mixture formed instantaneously. After 15 minutes, the reaction mixture was quenched by slow addition of saturated aqueous sodium sulfite solution and neutralized with saturated aqueous sodium carbonate solution. The mixture became colorless and was concentrated in vacuo to remove most of the acetone solvent. The resulting material was diluted with 400 mL of water and extracted with three 400 mL portions of diethyl ether. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford (S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol as a yellow oil (31.0 g, 100%).

Provenance & Evidence