Hydrochloric Acid → HCID 86684908, compound

4-(2,2,2-Trifluoro-ethoxy)-2-trifluoromethyl-1-tritylsulfanyl-benzene (100 g, 193 mmol) was dissolved in dichloromethane (600 mL) and trifluoroacetic acid (44.9 g, 386 mmol) was added at room temperature, followed by a solution of triethylsilane (24.9 g, 214 mmol) in dichloromethane (75 mL) at 18° C. (ice bath cooling). The yellow mixture was stirred for 3 h at room temperature. Water (600 mL) was then added and dichloromethane was distilled off in vacuo under vigorous stirring. Tert-butyl-methylether (600 mL) was added and the resulting biphasic mixture was basified by addition of a concentrated aqueous sodium hydroxide solution (32% m/m, 54 mL, 583 mmol) to pH 12. Phases were separated, the aqueous layer was extracted with tert-butyl-methylether (400 mL), acidified by addition of hydrochloric acid (25% m/m in water, 35 mL, 268 mmol) to pH 3, and extracted with tert-butyl-methylether (600 mL). The organic extract was washed with a solution of sodium hydrogencarbonate (16.1 g, 193 mmol) in water (500 mL), and water (500 mL) and concentrated in vacuo to afford the title compound as a light yellow liquid (49.7 g, 90%). MS (ESI & APCI, neg): m/z=275.0 [M−H]+. 1H NMR (CDCl3, 600 MHz): δ3.66 (q, J=2.5 Hz, 1H), 4.36 (q, J=8.0 Hz, 2H), 6.99 (dd, J=2.9 Hz, 8.6 Hz, 1H), 7.23 (d, J=2.8 Hz, 1H), 7.39 (d, J=8.6 Hz, 1H).

1. temperature(ice bath cooling)
2. distillationdichloromethane was distilled off in vacuo under vigorous stirring
3. additionTert-butyl-methylether (600 mL) was added
4. customPhases were separated
5. extractionthe aqueous layer was extracted with tert-butyl-methylether (400 mL)
6. extractionextracted with tert-butyl-methylether (600 mL)
7. extractionThe organic extract
8. concentrationconcentrated in vacuo

ORD record

ord-a4d8c6d17f4f471495d85e71a04b5230

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796471B2