tert-Butyldimethylsilyl chloride → HCID 58026128, compound

Temperature

0 °C

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.

1. stirringThe reaction mixture was stirred at room temperature for 24 hours
2. concentrationThe reaction mixture was then concentrated
3. additiondiluted with 500 mL of ethyl acetate
4. washwashed with 100 mL of saturated sodium bicarbonate solution
5. customThe organic phase was separated
6. washwashed with 100 mL of water, 100 mL of brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude mixture was purified by flash chromatography
11. washThe column was eluted with hexane

ORD record

ord-077d6ddf447044c9b52761708626caa5

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268859B2