Benzoyl Peroxide → HCID 67530139, compound

HRID 2388202Notes

Reaction equation

HRID 2388202 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:10]([CH3:11])=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][N:7]=1.C1C(=O)N([Br:24])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:24][C:5]1[O:1][C:2]([C:6]2[C:10]([CH3:11])=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][N:7]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67531351HCID 67531351, compound

Product 1

HCID 67530139HCID 67530139, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 3-(furan-2-yl)-4-methylisoxazole-5-carboxylate (5.8 g, 26.2 mmol), NBS (5.6 g, 31.5 mmol), and benzoyl peroxide (0.64 g, 2.62 mmol) were added to 150 mL of carbon tetrachloride and the mixture was refluxed for 16 h. Reaction mixture was filtered and concentrated. The residue was purified by flash chromatography (0-30% EtOAc/hexanes) to give 1.7 g of the title compound. MS: (+) m/z 300.31, 322.28 (M+1, 79Br/81Br).

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. customReaction mixture
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2efda1c40d104730933d31fccd9dfa46
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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