Azobisisobutyronitrile → 2-(Bromomethyl)-3-chlorobenzonitrile

HRID 1681941

Reaktionsgleichung

Reaktionsgleichung von HRID 1681941
[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-3b546b47d34b473092825a58018d0021
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05175164

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