Azobisisobutyronitrile → Methyl 2-(bromomethyl)benzoate

HRID 50143

Reaction equation

HRID 50143 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10].[Br:12]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>ClC(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][Br:12]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 33094Methyl o-toluateHCID 67184N-bromobutanimide

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methylbenzoic acid methyl ester (33.0 g) in tetrachlorocarbon (440 ml) were added N-bromosuccinimide (43.0 g) and AIBN (2,2′-azobisisobutyronitrile, 361 mg) and the mixture was refluxed for 30 minutes. The reaction mixture was cooled down to 0° C. and cinnamoic acid that appeared were filtered off and the filtrate was concentrated. The residue was purified by distillation under reduced pressure to give the title compound having the following physical data (28.0 g, colorless oil).

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. filtrationcinnamoic acid that appeared were filtered off
  3. concentrationthe filtrate was concentrated
  4. distillationThe residue was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-a96861900862401e895e29ef678b6cde
Source dataset
uspto-grants-2004_03
Patent number
US06710205B2

Linked notes

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