Azobisisobutyronitrile → HCID 53938046, compound

HRID 1250141Notes

Reaction equation

HRID 1250141 reaction equation
[CH3:1][C:2]1[CH:16]=[C:15](Cl)[CH:14]=[CH:13][C:3]=1[O:4][C:5](=[CH:10][O:11][CH3:12])[C:6]([O:8][CH3:9])=[O:7].[Br:18]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>>[Br:18][CH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][C:5](=[CH:10][O:11][CH3:12])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 53395499HCID 53395499, compound

Product 1

HCID 53938046HCID 53938046, compound

Procedure

A mixture of 5.13 g of methyl 2-(2-methyl-4-chlorophenoxy)-3-methoxyacrylate, 3.56 g of N-bromosuccinimide, and a catalytic amount of azobisisobutyronitrile was heated at reflux with light irradiation for 4 hours. The mixture was filtered through silica gel, and the solvent evaporated to give a crude sample of methyl 2-(2-bromomethylphenoxy)-3-methoxyacrylate. A mixture of this crude material and 2.46 g of sodium acetate in N,N-dimethylformamide was heated at 100 C. for 4 hours. Water was added and the mixture extracted with ethyl acetate, dried with anhydrous sodium sulfate, evaporated and the residue purified by silica gel column chromatography to give methyl 2-(2-acetyloxymethyl-4-chlorophenoxy)-3-methoxyacrylate) (3.2 g).

Workup

  1. temperatureat reflux with light irradiation for 4 hours
  2. filtrationThe mixture was filtered through silica gel
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-8a31cf1f7f2c477186268f4792ed7b0a
Source dataset
uspto-grants-2002_01
Patent number
US06337306B1

Reaction notes

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