Hexachloroethane → HCID 71226985, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added 5-(4-(trifluoromethoxy)phenyl)oxazole (3.49 g, 15.23 mmol) and THF (15 mL). The reaction was cooled to −78° C. Then 2.5 M nBuLi (6.70 mL, 16.75 mmol) was added to the reaction at −78° C. The reaction turned to deep red color. After 15 min, hexachloroethane (2.59 mL, 22.84 mmol) was added at −78° C. The reaction was slowly warmed to rt over 2 hrs. The reaction was then poured onto ice and extracted with EtOAc (2×30 ml). The combined EtOAc layers were washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give the product, 2-chloro-5-(4-(trifluoromethoxy)phenyl)oxazole, (2 g, 7.59 mmol, 49.8% yield) as a light orange liquid. Anal. Calcd. for C10H5F3NO2 m/z 263.1, found: 264.1 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 7.64 (s, 2 H), 7.30 (s, 4 H); 13C NMR (126 MHz, CDCl3) δ ppm 152.51, 149.41, 146.62, 125.57, 123.83, 121.41, 119.36.

Provenance & Evidence