Potassium Cyanide → (3-Chloro-2-methoxyphenyl)acetonitrile

HRID 1443179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443179
C1C(=O)[N:5](Br)[C:3](=O)C1.[Cl:9][C:10]1[C:11]([O:17][CH3:18])=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=1.[C-]#N.[K+]>C(Cl)(Cl)(Cl)Cl.O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:9][C:10]1[C:11]([O:17][CH3:18])=[C:12]([CH:13]=[CH:14][CH:15]=1)[CH2:16][C:3]#[N:5]

Komponenten

7

Edukt 3

HCID 9032Potassium CyanideHCID 67184N-bromobutanimideHCID 134345771-Chloro-2-methoxy-3-methylbenzene

Produkt 1

HCID 17989277(3-Chloro-2-methoxyphenyl)acetonitrileAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 7187Benzoyl PeroxideKatalysatorHCID 962WaterLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

39.4 g (221.3 mmol) of NBS and 100 mg of benzoyl peroxide are added to 31.6 g (201.7 mmol) of 3-chloro-2-methoxytoluene in 500 ml of CCl4. It is refluxed over 16 hours, allowed to cool and filtered. Solvent is removed from the filtrate, and the filtrate is dissolved in 214 ml of N,N-dimethylformamide and 142 ml of water. 20.9 g (322.1 mmol) of potassium cyanide is added at 0° C. and stirred over 16 hours. The reaction mixture is diluted with water and extracted several times with tert-butyl-methyl ether. The organic phase is washed several times with saturated sodium chloride solution and dried on sodium sulfate. The solvent is removed in a vacuum and after chromatographic purification on silica gel (hexane/ethyl acetate 20%), 29.7 g of product is obtained.

Aufarbeitung

  1. temperatureIt is refluxed over 16 hours
  2. temperatureto cool
  3. filtrationfiltered
  4. customSolvent is removed from the filtrate
  5. dissolutionthe filtrate is dissolved in 214 ml of N,N-dimethylformamide
  6. extractionextracted several times with tert-butyl-methyl ether
  7. washThe organic phase is washed several times with saturated sodium chloride solution
  8. customdried on sodium sulfate
  9. customThe solvent is removed in a vacuum
  10. customafter chromatographic purification on silica gel (hexane/ethyl acetate 20%)

Quellen und Nachweise

ORD-Eintrag
ord-d7f2d222afe14df4881643c7bc3ae2a3
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659297B2

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