2-Bromobenzaldehyde → 1-(2-Bromophenyl)-2,2,2-trifluoroethan-1-ol

The title compound was prepared by an adaptation of the method described in Xue, Y. et al. (Bioorg. Med. Chem. 2007, 15, 2156-2166). Tetrabutylammonium fluoride hydrate (0.05 eq., 131 mg, 0.050 mmol) was placed in a 40 mL vial equipped with a magnetic stir bar, and the vial was evacuated and backflushed with Ar. Dry THF (25 mL) was added via syringe, and 2-bromobenzaldehyde (1.16 mL, 10.0 mmol) and trimethylsilyltrifluoromethane (1.3 eq., 1.90 mL, 13.0 mmol) were sequentially added via syringe. The reaction was stirred at RT for 16 h, and additional CF3 TMS (1 mL) was added. After stirring for 2 h, the reaction was poured into 3 M aq HCl (30 mL) and stirred at RT for 2 h. The reaction mixture was extracted three times with DCM (30 mL), and the combined organic extracts were dried over anhydrous MgSO4, filtered, and the solvent removed under reduced pressure, yielding 1.83 g (72%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 7.69 (d, J=7.8 Hz, 1H), 7.60 (dd, J=8.1, 1.3 Hz, 1H), 7.40 (td, J=7.6, 1.1 Hz, 1H), 7.27 (td, J=7.7, 1.8 Hz, 1H), 5.56-5.68 (m, 1H), 2.77 (d, J=4.8 Hz, 1H).

1. customThe title compound was prepared by an adaptation of the method
2. customvial equipped with a magnetic stir bar
3. customthe vial was evacuated
4. additionDry THF (25 mL) was added via syringe
5. stirringAfter stirring for 2 h
6. stirringstirred at RT for 2 h
7. extractionThe reaction mixture was extracted three times with DCM (30 mL)
8. dry with materialthe combined organic extracts were dried over anhydrous MgSO4
9. filtrationfiltered
10. customthe solvent removed under reduced pressure

ORD record

ord-25de0d8e9834451ba92fd2ec7b2351a8

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232409B2