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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence