Hydroxyamine hydrochloride → HCID 76540720, compound

HRID 2060749Notes

Reaction equation

HRID 2060749 reaction equation
[CH2:1]([O:4][CH2:5][C:6]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[F:15])=O)[CH:2]=[CH2:3].Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>C(O)C>[CH2:1]([O:4][CH2:5][C:6]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[F:15])=[N:17][OH:18])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 574757622-(Allyloxy)-1-(5-bromo-2-fluorophenyl)ethanone

Product 1

HCID 76540720HCID 76540720, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(allyloxy)-1-(5-bromo-2-fluorophenyl)ethanone (118 g, 432.1 mmol) in ethanol (1.7 L) is added hydroxylamine hydrochloride (34.5 g, 496.9 mmol) and sodium ethanoate (40.8 g, 496.9 mmol) at 25° C. The reaction is heated at 70° C. for 1 hr. The reaction is cooled and the solvent is removed under reduced pressure. The residue is washed with water (1 L) and is extracted three times with dichloromethane (3×500 mL). The organic phase is dried over magnesium sulfate, filtered, and the solvent is removed under reduced pressure, to obtain the title compound as a mixture of two possible oximes (120 g, 96%). ES/MS m/e (79Br/81Br) 288, 290 (M+1).

Workup

  1. temperatureThe reaction is cooled
  2. customthe solvent is removed under reduced pressure
  3. washThe residue is washed with water (1 L)
  4. extractionis extracted three times with dichloromethane (3×500 mL)
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-83adc85bc82e4ca2ac37e0fc8bc1e496
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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