Azobisisobutyronitrile → Methyl 4-(bromomethyl)-3-chlorobenzoate

HRID 227222Notes

Reaction equation

HRID 227222 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].C1C(=O)N([Br:20])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 2801405Methyl 3-Chloro-4-methylbenzoate

Product 1

HCID 22027761Methyl 4-(bromomethyl)-3-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl 3-chloro-4-methylbenzoate (5.0 g, 27.1 mmol) in carbon tetrachloride (50 ml) were added NBS (5.8 g, 32.0 mmol) and AIBN (0.442 g, 2.70 mmol). The mixture was stirred at reflux for 18 h. The mixture was allowed to cool to room temperature and then concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 0:100 to 5:95); yield 5.96 g (84%).

Workup

  1. temperatureat reflux for 18 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 0:100 to 5:95)

Sources & evidence

ORD record
ord-24ae167fc57f4315a13dab347ebcdfad
Source dataset
uspto-grants-2009_07
Patent number
US07560454B2

Reaction notes

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