Sodium Iodide → (S)-4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol

Participants

Reaction Steps

To a suspension of (S)-4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-((R)-toluene-4-sulfinylmethyl)pentan-2-ol (11.5 g, 22.8 mmol) and sodium iodide (10.2 g, 68.1 mmol) in 180 mL of anhydrous acetone at −40° C. was added a solution of trifluoroacetic acid anhydride (16.0 mL, 113 mmol) in 30 mL of anhydrous acetone dropwise by syringe over 20 minutes. A greenish brown mixture was formed instantaneously. After 20 minutes, the reaction mixture was quenched with saturated aqueous sodium sulfite solution and neutralized with saturated aqueous sodium carbonate solution. The brown color disappeared and the crude was concentrated to remove most of the acetone solvent. The resulting material was diluted with 350 mL of water and extracted with three 600 mL portions of ether. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford (S)-4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethyl-pentan-2-ol as a yellow oil (11.1 g, 99%).

Provenance & Evidence