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

HRID 343964Notes

Reaction equation

HRID 343964 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 azobisiso-butyronitrile (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-26a5b0d63efe451aab8d09bee8e8962a
Source dataset
uspto-grants-1999_01
Patent number
US05863930

Reaction notes

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