Azobisisobutyronitrile → Methyl 5-bromo-2-(bromomethyl)benzoate

HRID 730170Notes

Reaction equation

HRID 730170 reaction equation
[Br:1]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[CH3:21][O:22][C:23](=[O:33])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26](Br)[C:25]=1[CH2:31][Br:32]>C(Cl)(Cl)(Cl)Cl>[CH3:21][O:22][C:23](=[O:33])[C:24]1[CH:29]=[C:28]([Br:1])[CH:27]=[CH:26][C:25]=1[CH2:31][Br:32]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 21907554Methyl 3-bromo-2-(bromomethyl)benzoate

Product 1

HCID 12929136Methyl 5-bromo-2-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The mixture of 3- and 5-bromo-2-methylbenzoic acid methyl ester (35.79 g; 156 mmol) is dissolved in carbon tetrachloride (200 mL). To the solution is added N-bromosuccinimide (29.5 g; 166 mmol), followed by AIBN (54 mg) and the mixture was heated at reflux temperature for 20 hours. Then the mixture was cooled to room temperature and the succinimide was filtered from solution and rinsed with carbon tetrachloride. The solvent was evaporated to yield a mixture of the title compound and 3-bromo-2-bromomethylbenzoic acid methyl ester (48.1 g; crude mass).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 20 hours
  3. filtrationthe succinimide was filtered from solution
  4. washrinsed with carbon tetrachloride
  5. customThe solvent was evaporated
  6. customto yield

Sources & evidence

ORD record
ord-53d15ff730b04c17928a0a6c7177c10c
Source dataset
uspto-grants-2009_09
Patent number
US07582667B2

Reaction notes

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