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

HRID 558111ノート

反応式

HRID 558111 の反応式
[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]

参加物

7

反応物 3

HCID 787HydroxylamineHCID 962WaterHCID 750602'-Bromoacetophenone

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 312751,4-Dioxane溶媒HCID 21906603Chloroform isopropyl alcohol溶媒

反応条件

温度
150 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-7cf66e0c305c43e4924391d5750a8c37
出典データセット
uspto-grants-2011_11
特許番号
US08063035B2

反応ノート

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