Azobisisobutyronitrile → 2-(Bromomethyl)-3-chlorobenzonitrile

HRID 1886463

Reaktionsgleichung

Reaktionsgleichung von HRID 1886463
[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[Br:11]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[C:3]=1[CH2:10][Br:11]

Komponenten

6

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5215083-Chloro-2-methylbenzonitrile

Produkt 1

HCID 149805102-(Bromomethyl)-3-chlorobenzonitrileAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943Carbon TetrachlorideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a refluxing solution of 3-chloro-2-methylbenzonitrile (2.0 g, 13.2 mmol) in 20 mL of CCl4 was added 2.6 g (14.4 mmol, 1.1 eq) of N-bromosuccinimide and 0.2 g of AIBN. The solution was refluxed for 3 hours and then cooled, diluted with 500 mL of CH2Cl2 and washed with 200 mL of H2O and 200 mL of brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resultant oil was flash chromatographed with 5:1 hexane/ethyl acetate to yield the titled compound (1.4 g, 46%) as a yellow oil.

Aufarbeitung

  1. temperatureThe solution was refluxed for 3 hours
  2. temperaturecooled
  3. washwashed with 200 mL of H2O and 200 mL of brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customchromatographed with 5:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4280b87baf5245388b53ad9905af87bd
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05151435

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