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 THF (20 mL) under nitrogen was added a solution of TBAF (1.3 g, 4.8 mmol) in THF (5 mL) dropwise at −30° C. The resulting solution was stirred at −30° C. for 1 hour and at ambient temperature for an additional 1 hour before 1 N aqueous HCl (10 mL) was added. The mixture was vigorously stirred at ambient temperature for 10 minutes, and then extracted with EtOAc (3×30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel (eluting with 1-3% EtOAc/hexane) to the title compound as a yellow oil. 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). MS ESI: [M+H]+ m/z 315.

1. additionwas added
2. extractionextracted with EtOAc (3×30 mL)
3. dry with materialThe combined organic layers were dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe crude residue was purified by MPLC on Silica gel (eluting with 1-3% EtOAc/hexane) to the title compound as a yellow oil

ORD record

ord-3e3525cde4f24a0187b6c4e770a5bb7b

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962608B2