Water → HCID 86684907, compound

Participants

Reaction Steps

Triphenylmethanol (39.7 g, 149.4 mmol) was dissolved in the solution of crude 4-fluoro-2-trifluoromethyl-benzenethiol in dichloromethane (ca. 260 mL) of the preceding step and a solution of trifluoroacetic acid (21.2 g, 186 mmol) in dichloromethane (20 mL) was added at room temperature. After stirring for 15 h, the mixture was basified by subsequent addition of water (20 mL), concentrated aqueous sodium hydroxide solution (32% m/m, 26.9 g, 215 mmol) and water again (240 mL). Phases were separated, the aqueous layer was extracted with dichloromethane (100 mL) and the combined organic extracts concentrated in vacuo at 50° C. to a volume of ca. 330 mL. Ethanol (400 mL) was continuously added to the distillation, while the overall volume was kept constant (solvent exchange). The solution (ca. 300 mL) was allowed to cool to room temperature, crystallization started at 42° C. The suspension was stirred for 18 h at room temperature and for 1 h at 0° C. After filtration, the precipitate was washed with cold ethanol (100 mL) and dried in vacuo at 40° C. to give rise to the title compound as a white crystalline solid (52.5 g, 79%). MS (EI): m/z=243 [CPh3]+. 1H NMR (CDCl3, 600 MHz): δ 6.73 (ddd, J=2.8 Hz, 8.3 Hz, 8.3 Hz, 1H), 7.04 (dd, J=5.4 Hz, 8.8 Hz, 1H), 7.18-7.25 (m, 10H), 7.35-7.37 (m, 6H). Anal. Calcd for C26H18F4S: C, 71.22; H, 4.14; S, 7.31; F, 17.33. Found: C, 71.16; H, 4.26; S, 7.15; F, 17.09.

Provenance & Evidence