N-bromobutanimide → HCID 15598728, compound

HRID 1905051Notes

Reaction equation

HRID 1905051 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[C:13]([O:15][C:16](=[O:18])[CH3:17])[CH:12]=[C:11]2[C:6]=1[C:7](=[O:28])[C:8]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[C:9]([CH3:19])[O:10]2)(=[O:3])[CH3:2].[Br:29]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:14]=[C:13]([O:15][C:16](=[O:18])[CH3:17])[CH:12]=[C:11]2[C:6]=1[C:7](=[O:28])[C:8]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)=[C:9]([CH2:19][Br:29])[O:10]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1535496HCID 1535496, compound

Product 1

HCID 15598728HCID 15598728, compoundYield 111.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 5,7-diacetoxy-4'-methoxy-2-methylisoflavone (2 g), benzoyl peroxide (0.1 g) and N-bromosuccinimide (1.4 g) in 120 ml carbon tetrachloride was heated under reflux for 20 hours, the solvent was distilled off under reduced pressure, and the solid residue was treated with water. The crude product collected by filtration was recrystallized from methanol, affording 2.7 g of 5,7-diacetoxy-4'-methoxy-2-bromomethylisoflavone.

Workup

  1. temperatureunder reflux for 20 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionthe solid residue was treated with water
  4. filtrationThe crude product collected by filtration
  5. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-2e945065235d4c879ddbdb5de40db57d
Source dataset
uspto-grants-1989_06
Patent number
US04841077

Reaction notes

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