(Trifluoromethyl)trimethylsilane → 1-(5-Bromopyridin-2-yl)-2,2,2-trifluoroethan-1-ol

5-Bromopicolinaldehyde (500 mg, 2.70 mmol) was dissolved in THF (9.0 mL) and the flask was then sealed with a septum, flushed with argon, and cooled to 0° C. (Trifluoromethyl)trimethylsilane (0.44 mL, 3.0 mmol) was then added followed by TBAF (2.7 mL, 2.7 mmol, 1M in THF). The resulting mixture was allowed to warm to ambient temperature and was stirred for 2 hours. The reaction was then quenched with water and extracted with DCM (2×). The combined organic extracts were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 10-20% EtOAc/hexanes) to afford the title compound. LRMS (ESI) calc'd for C8H6BrF3O [M+H]+: 256. Found: 256.

1. customthe flask was then sealed with a septum
2. customflushed with argon
3. additionwas then added
4. customThe reaction was then quenched with water
5. extractionextracted with DCM (2×)
6. washThe combined organic extracts were washed with brine
7. dry with materialdried over anhydrous MgSO4
8. concentrationconcentrated in vacuo
9. customThe residue was purified by MPLC on silica gel (
10. washa gradient elution of 10-20% EtOAc/hexanes)

ORD record

ord-99f8308bcd8a4a9fa6b713fbb3d3a5f3

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394282B2