Sodium Cyanide → m-Chlorophenylacetonitrile

HRID 254809

Reaktionsgleichung

Reaktionsgleichung von HRID 254809
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[C-:10]#[N:11].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C:10]#[N:11])[CH:7]=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 698381-(Bromomethyl)-3-chlorobenzene

Produkt 1

HCID 73722m-ChlorophenylacetonitrileAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The experimental procedure was followed by the method of Bruno P. Imbimbo et al [J. Med. Chem. 2005, 48, 5707-7520]. A solution of 3-chlorobenzylbromide (5 g, 24.3 mmol) and sodium cyanide (1.3 g, 26.8 mmol) in ethanol (50 ml) was heated to 80° C. for 2 hours. After resulting solution was cooled to room temperature and concentrated under reduced pressure. The residue was suspended in water and organic layer was extracted with ethyl acetate. The solution was evaporated and crude compound was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to yield 2-(3-chlorophenyl)acetonitrile (3.2 g, 87% yield) as colorless oil.

Aufarbeitung

  1. customAfter resulting solution
  2. concentrationconcentrated under reduced pressure
  3. extractionorganic layer was extracted with ethyl acetate
  4. customThe solution was evaporated
  5. customcrude compound was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-8947ee673ebb41428f9ec878f3d5b2cd
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875647B2

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