Azobisisobutyronitrile → Methyl alpha-[4-(3-bromomethylphenoxy)-6-methoxy-5-pyrimidinyl]-beta-methoxyacrylate

HRID 1957170Notes

Reaction equation

HRID 1957170 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][C:6]1[C:11]([C:12](=[CH:17][O:18][CH3:19])[C:13]([O:15][CH3:16])=[O:14])=[C:10]([O:20][CH3:21])[N:9]=[CH:8][N:7]=1.[Br:25]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:25][CH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][C:6]1[C:11]([C:12](=[CH:17][O:18][CH3:19])[C:13]([O:15][CH3:16])=[O:14])=[C:10]([O:20][CH3:21])[N:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 57241123Methyl alpha-[4-(3-methylphenoxy)-6-methoxy-pyrimidin-5-yl)-beta-methoxyacrylate

Product 1

HCID 53821122Methyl alpha-[4-(3-bromomethylphenoxy)-6-methoxy-5-pyrimidinyl]-beta-methoxyacrylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl α-[4-(3-methylphenoxy)-6-methoxy-pyrimidin-5-yl]-β-methoxyacrylate (2.7, 8.4 mmol), N-bromosuccinimide (1.6 g, 6 mmol) and a catalytic amount of AIBN are refluxed in CCl4 for 90 minutes. Filtration of the succinimide and evaporation of the solvent gives the methyl α-[4-(3-bromomethylphenoxy)-6-methoxy-pyrimidin-5-yl]-β-methoxyacrylate as a colorless oil.

Workup

  1. filtrationFiltration of the succinimide and evaporation of the solvent

Sources & evidence

ORD record
ord-c7db5a6ff94e452392dc8b03caefc779
Source dataset
uspto-grants-1998_07
Patent number
US05783580

Reaction notes

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