(Trifluoromethyl)trimethylsilane → HCID 86691229, compound

Participants

Reaction Conditions

Reaction Steps

Add neat (trifluoromethyl)trimethylsilane (109 mL, 0.74 mol) at 0° C. to a stirred solution of tetrabutylammonium acetate (88 g, 0.29 mol) and (N—Z)—N-[(4-bromophenyl)methylene]-(R)-2-methyl-propane-2-sulfinamide (85 g, 0.29 mol) in dimethylformamide (1.2 L) at 0° C. Stir the mixture at 0-5° C. for 90 minutes. Add saturated aqueous ammonium chloride solution (1.2 L) and extract with EtOAc (4×400 mL). Combine and sequentially wash the organic phase with water then brine (2×1 L); dry over magnesium sulphate; filter; and concentrate the filtrate under vacuum. Triturate the residue with hexane (200 mL) for 10 minutes, filter and dry the filtrate under vacuum to afford the title compound as a yellow solid (81 g, 76% yield, >98 de). MS (m/z): 358 (M+1).

Provenance & Evidence