Benzoyl Peroxide → 4',5,7-Triacetoxy-2-bromomethylisoflavone

HRID 1087960Notes

Reaction equation

HRID 1087960 reaction equation
[C:1]([O:4][C:5]1[CH:30]=[CH:29][C:8]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][C:14]([O:24][C:25](=[O:27])[CH3:26])=[CH:15][C:16]=3[O:20][C:21](=[O:23])[CH3:22])[O:11][C:10]=2[CH3:28])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:49]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:30]=[CH:29][C:8]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][C:14]([O:24][C:25](=[O:27])[CH3:26])=[CH:15][C:16]=3[O:20][C:21](=[O:23])[CH3:22])[O:11][C:10]=2[CH2:28][Br:49])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 221643584',5,7-Triacetoxy-2-methylisoflavone

Product 1

HCID 155987304',5,7-Triacetoxy-2-bromomethylisoflavoneYield 72.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 4',5,7-triacetoxy-2-methylisoflavone (5 g), benzoyl peroxide (0.3 g) and N-bromosuccinimide (3.9 g) in 300 ml carbon tetrachloride was heated under reflux for 12 hours, the solvent was distilled off under reduced pressure, water was added to the solid residue, the mixture was stirred well, and the crude product collected by filtration was recrystallized from a methanol/chloroform mixed solvent, affording 4.3 g of 4',5,7-triacetoxy-2-bromomethylisoflavone.

Workup

  1. temperatureunder reflux for 12 hours
  2. distillationthe solvent was distilled off under reduced pressure, water
  3. additionwas added to the solid residue
  4. filtrationthe crude product collected by filtration
  5. customwas recrystallized from a methanol/chloroform mixed solvent

Sources & evidence

ORD record
ord-e7ea8f61408f448faa521af0743a4d5e
Source dataset
uspto-grants-1990_10
Patent number
US04960908

Reaction notes

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