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

HRID 1631940Notes

Reaction equation

HRID 1631940 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11].[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:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 99590Methyl 2-methoxybenzeneacetate

Product 1

HCID 14234296Methyl 2-bromo-2-(2-methoxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 14.6 g (81.2 mmol) of methyl (2-methoxyphenyl)acetate, 15.2 g (85.3 mmol) of N-bromosuccinimide and a catalytic amount of AIBN in tetrachloromethane (180 ml) was heated under reflux with stirring for 2 h. The cooled reaction solution was filtered, and the solvent was removed in vacuo. Yield: 21.6 g (100%) of yellow oil

Workup

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

Sources & evidence

ORD record
ord-113e451f19ec423f8deb61e9fe412a17
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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