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

HRID 1905052Notes

Reaction equation

HRID 1905052 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-f17453f6de854d85819db5fe3188a466
Source dataset
uspto-grants-1989_06
Patent number
US04841077

Reaction notes

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