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

HRID 1400011Notes

Reaction equation

HRID 1400011 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

Conditions

Temperature
64 °C

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

Sources & evidence

ORD record
ord-ac757cd1706a4b5b91e8f6778859073c
Source dataset
uspto-grants-2014_12
Patent number
US08906914B2

Reaction notes

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