Azobisisobutyronitrile → HCID 53837103, compound

HRID 843973Notes

Reaction equation

HRID 843973 reaction equation
[Cl:1][C:2]1[C:3]([CH3:16])=[C:4]([C:8](=[CH:13][O:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Br:17]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>ClC(Cl)(Cl)Cl>[Br:17][CH2:16][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[C:8](=[CH:13][O:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 53931889HCID 53931889, compound

Product 1

HCID 53837103HCID 53837103, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
25 °C

Procedure

27.0 g of methyl α-(3-chloro-2-methylphenyl)-β-methoxy-acrylate and 21.5 g of N-bromosuccinimide were stirred in 300 ml of anhydrous tetrachloromethane. After 1 g of Porofor N had been added, the mixture was refluxed for 4 hours. After cooling to room temperature (=25° C.), the succinimide was removed. The combined organic phases were washed with water, dried over sodium sulfate and concentrated. This gave 23 g of the title compound as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customthe succinimide was removed
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-17c4a22d798e42e5862cfcdc384c8b6d
Source dataset
uspto-grants-2002_04
Patent number
US06380231B1

Reaction notes

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