Hydroxyamine hydrochloride → 2-Chloro-2',4'-difluoroacetophenone oxime

HRID 1374832Notes

Reaction equation

HRID 1374832 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=O.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][CH2:2][C:3](=[N:14][OH:15])[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 5880832-Chloro-1-(2,4-difluorophenyl)ethanone

Product 1

HCID 734116792-Chloro-2',4'-difluoroacetophenone oximeYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-2′,4′-difluoroacetophenone (3.09 g, 16.2 mmol) was dissolved in ethanol (30 ml). The solution was added under ice-cooling successively with hydroxylamine hydrochloride (1.23 g, 17.7 mmol) and sodium acetate (1.45 g, 17.7 mmol), and the mixture was allowed to warm to room temperature and stirred for 20 hours. The reaction solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate and washed with an aqueous sodium bicarbonate solution and then with saturated brine, and dried over magnesium sulfate. Insoluble solids were removed by filtration, and the solvent was evaporated under reduced pressure. The residue was suspended in hexane and dried to obtain the title compound as colorless solid (2.29 g, yield: 69%).

Workup

  1. additionThe solution was added under ice-
  2. customThe reaction solvent was evaporated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with an aqueous sodium bicarbonate solution
  5. dry with materialwith saturated brine, and dried over magnesium sulfate
  6. customInsoluble solids were removed by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customdried

Sources & evidence

ORD record
ord-02a3a08106614807bd577da299ba83b6
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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