Azobisisobutyronitrile → Methyl 3-bromo-2-(bromomethyl)benzoate

HRID 1059262Notes

Reaction equation

HRID 1059262 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[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:1][C:2]1[C:3]([CH2:12][Br:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 12929135Methyl 3-Bromo-2-methylbenzoate

Product 1

HCID 21907554Methyl 3-bromo-2-(bromomethyl)benzoateYield 96%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 3-bromo-2-methylbenzoate (1.00 g), N-bromosuccinimide (855 mg) and 2,2′-azobis(isobutyronitrile) (71.8 mg) in carbon tetrachloride (50 ml) was heated under reflux for 8 h. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chomatography (eluent; hexane:ethyl acetate=20:1) to give the title compound (1.29 g) as a colorless oil.

Workup

  1. temperatureunder reflux for 8 h
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chomatography (eluent; hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-8c5f9ae5e1e34538a80f9c2a9c34f2b0
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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