Ethanol → 4-Bromo-3-formylbenzonitrile

HRID 554589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 554589
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 225749024-Bromo-3-formylbenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f229cff590ee43e1bebf441db5d35dfd
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08049015B2

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