Hydrochloric Acid → HCID 59729402, compound

Participants

Reaction Steps

To a 0° C. solution of 3-fluoro-4-(2-methoxy-vinyl)-4′-trifluoromethyl-biphenyl (458 mg, 1.54 mmol) in THF (15 mL) is added dropwise concentrated hydrochloric acid (2.75 mL) and the reaction is warmed to room temperature. After 1 h TLC (30% EtOAc/hexane) indicates complete consumption of starting material. The reaction mixture was diluted with water and the pH is adjusted to 8 with solid NaHCO3. The reaction mixture is concentrated and the aqueous layer extracted with EtOAc (3×50 mL). The combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated and chromatographed (40 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (388 mg, 89%). 1NMR (400 MHz, CDCl3) δ ppm: 9.82 (s, 1H), 7.69 (q, 4H, J=8.4 Hz), 7.39 (dd, 1H, J=7.9, 1.3 Hz), 7.35 (dd, 1H, J=10.4, 1.5 Hz), 7.30 (t, 1H, J=7.7 Hz), 3.82 (s, 2H).

Provenance & Evidence