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

HRID 468803Notes

Reaction equation

HRID 468803 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].[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][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-chlorobenzoateYield 19%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl 3-chloro-4-methylbenzoate (920 mg, 5.0 mmol) in carbon tetrachloride (10 mL) were added N-bromosuccinimide (1.067 g, 6.0 mmol) and 2,2′-Azobis(2-methylpropionitrile) (81 mg, 0.50 mmol). The mixture was stirred at reflux overnight. The mixture was cooled to room temperature and concentrated. The residue was purified by column chromatography (Hexanes:ethyl acetate=10:1) to give the desired product (200 mg, 19%).

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (Hexanes:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-807381ba9be84379bcada545bc8a5902
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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