Ethanol → 4-Bromo-3-formylbenzonitrile

HRID 554589ノート

反応式

HRID 554589 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 225749024-Bromo-3-formylbenzonitrile

試薬・触媒・溶媒 2

HCID 24470Silver Nitrate触媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f229cff590ee43e1bebf441db5d35dfd
出典データセット
uspto-grants-2011_11
特許番号
US08049015B2

反応ノート

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