Ethanol → 4-Bromo-3-formylbenzonitrile

HRID 554589노트

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HRID 554589 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH:10](Br)Br.CC[OH:15]>O.[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH:10]=[O:15]

참가 물질

5

반응물 2

HCID 702EthanolHCID 159400004-Bromo-3-(dibromomethyl)benzonitrile

생성물 1

HCID 225749024-Bromo-3-formylbenzonitrile

시약·촉매·용매 2

HCID 24470Silver Nitrate촉매HCID 962Water용매

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온도
60 °C

실험 절차

4-Bromo-3-dibromomethyl-benzonitrile (5.66 g, 16 mmol) was dissolved in EtOH (150 mL) and heated to 60° C. Silver nitrate (6.80 g, 40 mmol), prepared as a solution in H2O (40 mL), was added dropwise, and the reaction was heated to 75° C. and stirred overnight. The organic layer was decanted, concentrated, and filtered, and the residue was partitioned between EtOAc and H2O. The product was extracted with EtOAc, and the combined organic layers were concentrated and purified by silica gel chromatography (0-30% EtOAc in hexanes) to give 4-bromo-3-formyl-benzonitrile.

후처리

  1. additionwas added dropwise
  2. temperaturethe reaction was heated to 75° C.
  3. customThe organic layer was decanted
  4. concentrationconcentrated
  5. filtrationfiltered
  6. customthe residue was partitioned between EtOAc and H2O
  7. extractionThe product was extracted with EtOAc
  8. concentrationthe combined organic layers were concentrated
  9. custompurified by silica gel chromatography (0-30% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-f229cff590ee43e1bebf441db5d35dfd
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08049015B2

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