(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-f82f2aecd7d046a7b0a9f1542457b83f

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962608B2