Azobisisobutyronitrile → Methyl 2-bromo-2-(3-methoxyphenyl)acetate

HRID 1631944Notes

Reaction equation

HRID 1631944 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=1.[Br:14]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>ClC(Cl)(Cl)Cl>[Br:14][CH:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 519609Methyl 2-(3-methoxyphenyl)acetate

Product 1

HCID 289522Methyl 2-bromo-2-(3-methoxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 15.7 g (87.1 mmol) of methyl (3-methoxyphenyl)acetate, 16.3 g (91.5 mmol) of N-bromosuccinimide and a catalytic amount of AIBN in tetrachloromethane (150 ml) was heated under reflux with stirring for 2 h. The cooled reaction solution was filtered and the solvent was removed in vacuo.

Workup

  1. temperatureunder reflux
  2. customThe cooled reaction solution
  3. filtrationwas filtered
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cad8bf87d5a843978871652333710bd4
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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