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

HRID 558937Notes

Reaction equation

HRID 558937 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-8adbeaccfcbe4b69bbc402efd4baee10
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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