Hydrochloric Acid → 3-(4-Bromo-2-fluorophenyl)-1,1,1-trifluoro-3-methylbutan-2-ol

To a solution of 2-(4-bromo-2-fluorophenyl)-2-methylpropanal (2.4 g, 9.8 mmol) and trimethyl(trifluoromethyl)silane (2.8 g, 20 mmol) in tetrahydrofuran (20 mL) under nitrogen was added the solution of TBAF (1.3 g, 4.8 mmol) in tetrahydrofuran (5 mL) dropwise at −30° C. The resulting solution was stirred at −30° C. for 1 hour and at ambient temperature for additional 1 hour before the addition of 1 N hydrochloric acid aqueous solution (10 mL). The mixture was vigorously stirred at ambient temperature for 10 minutes, and then extracted with ethyl acetate (3×30 mL). All the organic solution was dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography with 1-3% ethyl acetate in hexane to afford the title compound as a yellow oil. MS ESI: [M+H]+ m/z 315; 1H NMR (300 MHz, CDCl3) δ 7.25-7.15 (m, 3H), 4.53 (q, J=7.5 Hz, 1H), 2.30 (br, 1H), 1.41 (s, 6H).

1. extractionextracted with ethyl acetate (3×30 mL)
2. dry with materialAll the organic solution was dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe crude residue was purified by flash column chromatography with 1-3% ethyl acetate in hexane

ORD record

ord-a9c8012ab4414ec7be5615a80c46ca89

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394282B2