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

HRID 2286356Notes

Reaction equation

HRID 2286356 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-6b7cdc4d21a547b68c508b77adbb132d
Source dataset
uspto-grants-1981_05
Patent number
US04265891

Reaction notes

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