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

HRID 558111

반응식

HRID 558111 반응식
[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]

참가 물질

7

반응물 3

HCID 787HydroxylamineHCID 962WaterHCID 750602'-Bromoacetophenone

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 312751,4-Dioxane용매HCID 21906603Chloroform isopropyl alcohol용매

반응 조건

온도
150 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-7cf66e0c305c43e4924391d5750a8c37
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063035B2

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