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

HRID 270920Notes

Reaction equation

HRID 270920 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.[CH3:13][O:14][C:15](=[O:25])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1.C1C(=O)N([Br:33])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[CH3:13][O:14][C:15](=[O:25])[CH:16]([Br:33])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1

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

AIBN (10 mg) was added to a solution of (3-Methoxy-phenyl)-acetic acid methyl ester (2 g, 11 mmol) in CCl4 (30 ml). The solution was then heated to reflux and NBS (2.3 g, 13 mmol) was added in portions. After complete addition the reaction mixture was refluxed for 4 h. After cooling, solid residue was filtered off and the filtrate concentrated to yield product Bromo-(3-methoxy-phenyl)-acetic acid methyl ester, that was washed repeatedly with pet ether.

Workup

  1. temperatureThe solution was then heated
  2. temperatureto reflux
  3. additionAfter complete addition the reaction mixture
  4. temperaturewas refluxed for 4 h
  5. temperatureAfter cooling
  6. filtrationsolid residue was filtered off
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-055cd0ad1a504888886fea879d7b9bcb
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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