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

HRID 647496

Reaction equation

HRID 647496 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 118166671-Azido-4-(bromomethyl)benzeneYield 104.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-40886f249d35446d8c2e81848d2ebd9e
Source dataset
uspto-grants-1983_10
Patent number
US04409213

Linked notes

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