Azobisisobutyronitrile → HCID 53667290, compound

HRID 1250138Notes

Reaction equation

HRID 1250138 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][C:6](=[CH:11][O:12][CH3:13])[C:7]([O:9][CH3:10])=[O:8].[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][C:6](=[CH:11][O:12][CH3:13])[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 54476628HCID 54476628, compound

Product 1

HCID 53667290HCID 53667290, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 9.6 g of methyl 2-(3-methylphenoxy)-3-methoxyacrylate, 8.0 g of N-bromosuccinimide and a catalytic amount of azobisisobutyronitrile was heated at reflux in carbon tetrachloride for 4 hours. After cooling, the solid was filtered, the filtrate evaporated, and purified by silica gel column chromatography to give methyl 2-(3-bromomethylphenoxy)-3-methoxyacrylate (6.5 g).

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was filtered
  3. customthe filtrate evaporated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-3171868009ba422093f98ec46262c61f
Source dataset
uspto-grants-2002_01
Patent number
US06337306B1

Reaction notes

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