5'-Bromo-2'-hydroxyacetophenone → 1-(5-Bromo-2-hydroxyphenyl)ethanone oxime

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.Cl.[NH2:13][OH:14].C([O-])(=O)C.[K+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6](/[C:8](=[N:13]/[OH:14])/[CH3:9])[CH:7]=1

Participants

Procedure

To a solution of 1-(5-bromo-2-hydroxyphenyl)ethanone (2.0 g, 9.30 mmol) in ethanol (20 mL) were added hydroxylamine hydrochloride (0.7 g, 10.2 mmol) and potassium acetate (1.0 g, 10.2 mmol). The mixture was stirred at reflux temperature for 16 h. After this time, the mixture was cooled, concentrated and the residue was diluted with CH2Cl2 (25 mL) and washed with H2O (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford title compound (11) (2.1 g, 95%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.40 (s, 1H), 7.20 (dd, J=8.8, 2.0 Hz, 1H), 6.72 (d, J=8.8 Hz, 1H), 2.50 (bs, 1H), 2.20 (s, 3H); MS (ESI, M+H+) C8H9BrNO2, calcd. 230.0. found 230.0, 232.0.