4-Nitrobenzaldehyde → 2,2,2-Trifluoro-1-(4-nitrophenyl)ethanol

Temperature

0 °C

A solution of 4-nitro-benzaldehyde (2.5 g, 17 mmol) in tetrahydrofuran (35 ml) was treated with trimethyl-trifluoromethyl-silane (2N in tetrahydrofuran, 10 ml, 20 mmol, 1.2 equiv.) and cooled to 0° C. A solution of tetrabutylammonium fluoride (1N in tetrahydrofuran, 1.70 ml, 2 mmol) was added, upon which the solution turned bright orange and then black. The mixture was stirred at 0° C. for 10 min, then at room temperature for 1 hour. The mixture was quenched with HCl 3N (6 ml), and stirred at room temperature overnight. The reaction was then diluted with ethyl acetate and brine and the two phases separated. The organic phase was washed with water, dried with Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate gradient), yielding 2,2,2-trifluoro-1-(4-nitro-phenyl)-ethanol as a yellow solid, 2.1 g (57%). MS (ISP): m/e=220.1 (M−H), δH (300 MHz; CDCl3) 8.28 (2H, d), 7.70 (2H, d), 5.19 (1H, m), 2.84 (1H, d).

1. waitat room temperature for 1 hour
2. customThe mixture was quenched with HCl 3N (6 ml)
3. stirringstirred at room temperature overnight
4. additionThe reaction was then diluted with ethyl acetate and brine
5. customthe two phases separated
6. washThe organic phase was washed with water
7. dry with materialdried with Na2SO4
8. customthe solvent was evaporated
9. customThe residue was purified by flash chromatography (heptane/ethyl acetate gradient)

ORD record

ord-86bed354607a4536a97e2b7fa4db2e59

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07713996B2