Hydroxylamine → Ethanone, 1-(2-bromophenyl)-, oxime

HRID 558111

Reaction equation

HRID 558111 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH3:9].[NH2:11][OH:12].O>C(O)(=O)C.O1CCOCC1.C(Cl)(Cl)Cl.C(O)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:11][OH:12])[CH3:9]

Participants

7

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 750602'-Bromoacetophenone

Product 1

HCID 818696Ethanone, 1-(2-bromophenyl)-, oximeYield 83%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Conditions

Temperature
150 °C

Procedure

Combine 1-(2-bromo-phenyl)-ethanone (4.5 g, 22.6 mmol), 50% hydroxylamine in water (2.3 g, 69.6 mmol) and 1 mL of acetic acid in 15 mL of dioxane in a pressure vessel. Seal the vessel and heat the mixture in an oil bath for 3 h at 150° C. Cool the mixture to room temperature (RT). Dilute with chloroform/IPA (3/1), wash with water and aqueous saturated sodium chloride. Separate the layers and dry the organic layer over sodium sulfate. Concentrate in vacuo to give the crude product. Purify by column chromatography (20% THF in dichloromethane (DCM) to give the title compound (4.0 g, 83%). MS (ES) m/z 214/216 [M+1]+.

Workup

  1. customSeal the vessel
  2. temperatureCool the mixture to room temperature (RT)
  3. washwash with water and aqueous saturated sodium chloride
  4. customSeparate the layers
  5. dry with materialdry the organic layer over sodium sulfate
  6. concentrationConcentrate in vacuo
  7. customto give the crude product
  8. customPurify by column chromatography (20% THF in dichloromethane (DCM)

Sources & evidence

ORD record
ord-7cf66e0c305c43e4924391d5750a8c37
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Linked notes

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