Trifluoroacetic acid → HCID 86684906, compound

Participants

Reaction Steps

2-Chloro-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-1-tritylsulfanyl-benzene (220 g, 441 mmol) was dissolved in dichloromethane (800 mL) and trifluoroacetic acid (165 mL, 2.15 mol) was added at room temperature, followed by triethylsilane (110 mL, 674 mmol, ice bath cooling necessary). After stirring for 30 min at room temperature, the mixture was concentrated in vacuo. A potassium hydroxide solution (2M in water, 1.1 L) was added to the residue, and the suspension was stirred for 15 min. After filtration, the remaining solid was washed with water. The combined filtrate was acidified to pH<2 by addition of hydrochloric acid (25% in water, 330 mL) and extracted with tert-butyl-methylether (3×500 mL). The combined organic extracts were washed with an aqueous potassium hydrogencarbonate solution (1M, 330 mL), dried over sodium sulfate, and concentrated in vacuo. The turbid oil was treated with heptane (80 mL) and filtered. The remaining solid was further washed with heptane (20 mL). The combined filtrate was concentrated and dried in vacuo to yield the title compound as a colorless liquid (105 g, 93%). 1H NMR (CDCl3, 400 MHz): δ 1.49 (dd, J=6.5 Hz, 0.5 Hz, 3H), 3.75 (s, 1H), 4.55 (qq, J=6.2 Hz, 6.2 Hz, 1H), 6.79 (dd, J=3.0 Hz, 8.9 Hz, 1H), 7.03 (d, J=2.7 Hz, 1H), 7.29 (d, J=8.6 Hz, 1H).

Provenance & Evidence