Cesium fluoride → 7,8-Dichloro-1-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-ol

Participants

Reaction Conditions

Reaction Steps

7,8-Dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.2 g, 0.78 mmol) was dissolved in anhydrous THF (5 mL), cooled to 0° C., and CF3TMS (1.2 mL, 8.7 mmol) followed by CsF (0.36 mg, 2.3 mmol) were added and stirred for 30 min. at 0° C. The reaction mixture was slowly warmed to room temperature and stirred for an additional 2 h, quenched with saturated NH4Cl and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude compound which was purified by column chromatography [EtOAc-hexane (1:4) as eluant] to provide the title compound as a yellow syrup (0.05 g, 19%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.32 (bs, 1H), 7.38 (d, J=8.5 Hz, 1H), 7.21 (d, J=8.5 Hz, 1H), 2.85-2.81 (m, 1H), 2.73-2.70 (m, 1H), 2.68 (s, 1H), 2.29-2.24 (m, 1H), 2.13-2.11 (m, 2H), 2.03-2.01 (m, 1H).

Provenance & Evidence