Benzoyl Peroxide → HCID 19744428, compound

HRID 2254451Notes

Reaction equation

HRID 2254451 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][O:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>C(Cl)(Cl)(Cl)Cl>[O:11]1[CH:12]=[C:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[CH2:1][Br:13])[CH:9]=[N:10]1

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 19744760HCID 19744760, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 19744428HCID 19744428, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

185 mg of 4-(3-methylphenyl)isoxazole [see J. Heterocyclic Chem., 11, 51 (1974); and J. Chem. Soc., Perkin II, 1121 (1977)] was dissolved in 8 ml of carbon tetrachloride, and 206 mg of N-bromosuccinimide and a catalytic amount of benzoyl peroxide were added. The mixture was refluxed with stirring for 3 hours. The insoluble material was separated by filtration and the solvent was evaporated. The residue was purified by silica gel column chromatography Wakogel C-200, 30 g; eluting solvent: hexane/ethyl acetate=10/1 to give 210 mg (yield 76%) of the captioned compound as a colorless powder

Workup

  1. temperatureThe mixture was refluxed
  2. customThe insoluble material was separated by filtration
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography Wakogel C-200, 30 g

Sources & evidence

ORD record
ord-74431b9cfdfa47f09d2581cc44c831c1
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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