Azobisisobutyronitrile → 4-(Bromomethyl)-2-chloro-1-iodobenzene

HRID 234766Notes

Reaction equation

HRID 234766 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[I:8].[Br:10]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[I:8])[CH2:9][Br:10]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27576182-Chloro-1-iodo-4-methylbenzene

Product 1

HCID 542552924-(Bromomethyl)-2-chloro-1-iodobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 40.4 g (160 mmol) of the compound from Example XXXI in 400 ml of carbon tetrachloride, 31.3 g of N-bromosuccinimide (176 mmol) and 2.63 g of azobisisobutyronitrile (16 mmol) is heated under reflux overnight. After cooling, the precipitate is filtered off with suction and washed with carbon tetrachloride. The combined filtrates are concentrated and the residue is further reacted in the crude state.

Workup

  1. temperatureis heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. filtrationthe precipitate is filtered off with suction
  5. washwashed with carbon tetrachloride
  6. concentrationThe combined filtrates are concentrated
  7. customthe residue is further reacted in the crude state

Sources & evidence

ORD record
ord-2d9396fe463b42afb56f4077c7234a30
Source dataset
uspto-grants-1997_01
Patent number
US05596006

Reaction notes

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