Hydrochloric Acid → HCID 57658763, compound

Participants

Reaction Steps

[4-Bromo-2-(1-phenyl-1H-pyrazole-4-carbonyl)phenoxy]-acetonitrile (38 mg) was added NaN3 (66 mg), ZnBr2 (59 mg), isopropanol (1.3 mL) and water (1.6 mL), and the reaction mixture was heated to reflux for 1 h. The mixture was added 3% HCl (1 mL) and EtOAc (4 mL) and stirred until two clear phases appeared. The aqueous phase was added 3% HCl until pH<1 and extracted with EtOAc. The combined organic phases were washed with brine, dried (MgSO4) and concentrated to give 47 mg white foam: LC/MS (an10n8): Rt 2.93, m/z 243.0 [M−H]−; 1H NMR (CDCl3): δ 5.69 (s, 2H), 7.13 (d, J=8.6 Hz, 1H), 7.39-7.45 (m, 1H), 7.49-7.56 (m, 2H), 7.62-7.71 (m, 2H), 7.71-7.79 (m, 1H), 8.13 (s, 1H), 8.45 (s, 1H); 13C NMR (CDCl3): δ 63.3, 115.6, 117.7, 120.3, 124.5, 128.6, 130.0, 131.2, 132.0, 132.9, 136.3, 139.1, 143.5, 154.7, 188.4.

Provenance & Evidence