Benzoyl Peroxide → HCID 67530800, compound

HRID 2388249Notes

Reaction equation

HRID 2388249 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([CH2:11][CH3:12])[C:7]=1[CH3:13])=[O:5])[CH3:2].C1C(=O)N([Br:21])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([CH2:11][CH3:12])[C:7]=1[CH2:13][Br:21])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67531479HCID 67531479, compound

Product 1

HCID 67530800HCID 67530800, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-Ethyl-4-methyl-isoxazole-5-carboxylic acid ethyl ester (3.5 g, 19.1 mmol), NBS (3.4 g, 19.1 mmol), and benzoyl peroxide (0.46 g mg, 1.91 mmol) were added to 110 mL of carbon tetrachloride and the mixture was refluxed for 16 h. The mixture was cooled to room temperature and concentrated in vacuo. The crude product was purified by flash chromatography (0-10% EtOAc/hexanes) to give 1.03 g of the title compound. MS: (+) m/z 262.17, 264.14 (M+1, 79Br/81Br).

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by flash chromatography (0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-45e336055b7645a18fd671a2f006e7bd
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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