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

HRID 2194556Notes

Reaction equation

HRID 2194556 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

5

Reactant 3

HCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium Acetate

Product 1

HCID 1355380141-(5-Bromo-2-hydroxyphenyl)ethanone oximeYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. temperatureat reflux temperature for 16 h
  2. temperatureAfter this time, the mixture was cooled
  3. concentrationconcentrated
  4. additionthe residue was diluted with CH2Cl2 (25 mL)
  5. washwashed with H2O (25 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa8953a7f9bc40d7af1ec9b475f5136a
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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