Azobisisobutyronitrile → Methyl 2-(bromomethyl)benzoate
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethe mixture was refluxed for 30 minutes
- filtrationcinnamoic acid that appeared were filtered off
- concentrationthe filtrate was concentrated
- distillationThe residue was purified by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-758fd5ab4561413199a6b5d511976a5c
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196198B2
Reaction notes
Loading…