tert-Butyldimethylsilyl chloride → HCID 58026128, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added 4-(2-bromophenyl)-1,1,1-trifluoro-4-methylpentan-2-ol (1.76 g, 5.66 mmol) in 30 mL of dry THF at 0° C. under nitrogen, followed by the dropwise addition of a solution of 2 M lithium diisopropylamine in THF (5.7 mL, 11.4 mmol). The reaction mixture was stirred at 0° C. for 30 minutes, followed by the addition of tert-butyldimethylsilyl chloride (4.26 g, 28.3 mmol). The reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was then concentrated, diluted with 500 mL of ethyl acetate, and washed with 100 mL of saturated sodium bicarbonate solution. The organic phase was separated, washed with 100 mL of water, 100 mL of brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified by flash chromatography. The column was eluted with hexane to afford 875 mg (36%) of [3-(2-bromophenyl)-3-methyl-1-trifluoromethylbutoxy]-tert-butyldimethylsilane.

Provenance & Evidence