Azobisisobutyronitrile → 1-Azido-4-(bromomethyl)benzene

HRID 543668

Reaktionsgleichung

Reaktionsgleichung von HRID 543668
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:11])=[CH:6][CH:5]=1)=[N+:2]=[N-:3]

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 1374301-Azido-4-methylbenzene

Produkt 1

HCID 118166671-Azido-4-(bromomethyl)benzeneAusbeute 104,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of p-azidotoluene (3.9 g), N-bromosuccinimide (5.5 g) and azobisisobutyronitrile (1.0 g) in carbon tetrachloride (30 ml) was heated under reflux in the dark under nitrogen for 18 h. The reaction mixture was allowed to cool to room temperature and the solvent was removed in vacuo. The residue was dissolved in ether (50 ml) and filtered. Evaporation of solvent gave an oil (6.5 g) which was chromatographed on silica gel (200 g, Merck 7734). Elution with petroleum ether (b.p. 40°-60°) gave the title compound as an oil (2.37 g). I.R. (Neat) 2120 cm-1.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux in the dark under nitrogen for 18 h
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ether (50 ml)
  5. filtrationfiltered
  6. customEvaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-70bde106412540d581cbff7cdb81f2a9
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04447428

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