Hydroxyamine hydrochloride → 1-(4-Bromo-2-fluoro-phenyl)-2,2,2-trifluoro-ethanone oxime

HRID 1908237Notes

Reaction equation

HRID 1908237 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([F:12])([F:11])[F:10])=[C:4]([F:14])[CH:3]=1.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:16][OH:17])[C:9]([F:12])([F:11])[F:10])=[C:4]([F:14])[CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 517045Sodium Acetate2×HCID 669578641-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 866351391-(4-Bromo-2-fluoro-phenyl)-2,2,2-trifluoro-ethanone oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution consisting of 1-(4-bromo-2-fluoro-phenyl)-2,2,2-trifluoro-ethanone (3.12 g, 11.5 mmol) and MeOH (50 mL) were added hydroxylamine hydrochloride (4.00 g, 57.5 mmol) and sodium acetate (5.90 g, 71.9 mmol). The resulting mixture was heated at 64° C. for 19 h, at which time additional hydroxylamine hydrochloride (2.40 g, 34.5 mmol) and sodium acetate (3.54 g, 43.1 mmol) were added. Heating was continued for 24 h and the mixture was cool to rt and the mixture was filtered to remove solids. The filtrate was diluted with EtOAc (150 mL), washed with water (150 mL), dried (Na2SO4) and concentrated. The title compound was obtained as a 70:30 ratio of the E and Z oxime isomers (3.28 g, 100%).

Workup

  1. additionwere added
  2. temperatureHeating
  3. filtrationthe mixture was filtered
  4. customto remove solids
  5. additionThe filtrate was diluted with EtOAc (150 mL)
  6. washwashed with water (150 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-348e318dc1884dc79aff8b2f48b50ed3
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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