4-Bromophenyl cyclopropyl ketone → 1-(4-Bromophenyl)-1-cyclopropyl-2,2,2-trifluoroethanol

To a solution of (4-bromophenyl)(cyclopropyl)methanone (587 mg, 2.60 mmol) in tetrahydrofuran (5.2 mL) were added molecular sieves 4 Å (500 mg), trimethylsilyl trifluoromethane (772 μL, 5.20 mmol) and tetrabutylammonium fluoride (tetrahydrofuran solution, 1 mol/L, 3.9 mL, 3.90 mmol) at 0° C., and the mixture was stirred at room temperature for 18 hours. The solution was filtered through diatomaceous earth, and then thereto was added 1 mol/L hydrochloric acid solution (10 mL), and the mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→5:1) to give 1-(4-bromophenyl)-1-cyclopropyl-2,2,2-trifluoroethanol (747 mg, 97%) as a colorless oil.

1. filtrationThe solution was filtered through diatomaceous earth
2. additionwas added 1 mol/L hydrochloric acid solution (10 mL)
3. extractionthe mixture was extracted with ethyl acetate twice
4. washwashed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→5:1)

ORD record

ord-3b23c2ecdd284b12bd5d38c6d02ec7b8

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987445B2