Trifluoroacetic acid → HCID 58290283, compound

Participants

Reaction Steps

To a solution of commercially available 2,2,2-trifluoro-1-(2-fluoro-5-iodophenyl)ethanone (2 g, 6.29 mmol) in 20 mL dichloromethane at rt was added N,N-diisopropylethylamine (3.3 mL, 18.95 mmol, 3 eq.) followed by 1M solution of TiCl4 in dichloromethane (6.3 mL, 6.3 mmol, 1 eq.). The mixture was stirred at rt for 3 days, added 10 mL of methanol followed by NaCNBH3 (3.2 g) and trifluoroacetic acid (4.7 mL). The mixture was stirred overnight at rt, poured into aq. NaHCO3 and extracted 3× with dichloromethane. The combined organic layer was washed with brine, dried over MgSO4, filtered, concentrated and purified by chromatography eluting with 0% to 20% ethyl acetate in hexane to provide 1.16 g of MCH14-1.

Provenance & Evidence