Azobisisobutyronitrile → Methyl 4-(bromomethyl)-2-methoxybenzoate

HRID 278567Notes

Reaction equation

HRID 278567 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([O:2][CH3:1])[CH:12]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 7172021Methyl 2-methoxy-4-methylbenzoate

Product 1

HCID 11288398Methyl 4-(bromomethyl)-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 2-methoxy-4-methylbenzoate (5.0 g), N-bromosuccinimide (4.94 g), 2,2′-azobis(isobutyronitrile) (0.23 g) and carbon tetrachloride (50 ml) was heated for 40 minutes under reflux. The mixture was cooled and the precipitate was filtered off. The filtrate was concentrated to give methyl 4-bromomethyl-2-methoxybenzoate as an oil.

Workup

  1. temperaturewas heated for 40 minutes
  2. temperatureunder reflux
  3. temperatureThe mixture was cooled
  4. filtrationthe precipitate was filtered off
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-76376f28166749bf996dd6512fed7697
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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