5-Fluoro-2-nitrophenol → 4-Fluoro-1-nitro-2-(2,2,2-trifluoroethoxy)benzene

Participants

Reaction Steps

5-Fluoro-2-nitrophenol (3.07 g, 19.5 mmol) was dissolved in 50 mL of DMSO with cesium carbonate (7.62 g, 23.4 mmol) and stirred. 2,2,2-Trifluorethyl trifluoromethanesulfonate (5.00 g, 21.5 mmol) was added with 5 mL of DMSO. The reaction was stirred overnight and quenched with 50 mL of H2O. The mixture was poured into 1:1 diethyl ether/hexanes and H2O. The layers were separated, and the organic layer was washed with 10% K2CO3 (aqueous) (2×), H2O, and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford 2.95 g (63%) of the title compound of step A. 1H NMR (400 MHz, DMSO-d6) δ 8.06 (dd, J=9.0, 6.0 Hz, 1H), 7.45 (dd, J=10.7, 2.5 Hz, 1H), 7.08 (ddd, J=9.0, 7.9, 2.6 Hz, 1H), 4.97 (q, J=8.6 Hz, 2H).

Provenance & Evidence