Benzoyl Peroxide → HCID 67529296, compound

HRID 2388203Notes

Reaction equation

HRID 2388203 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]2[C:11]([CH3:12])=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:9][N:8]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:25])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[O:6][C:5]([C:7]2[C:11]([CH2:12][Br:25])=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67530139HCID 67530139, compound

Product 1

HCID 67529296HCID 67529296, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 3-(5-bromofuran-2-yl)-4-methylisoxazole-5-carboxylate (1.7 g, 5.67 mmol), NBS (1.2 g, 6.8 mmol), and benzoyl peroxide (0.14 g, 0.567 mmol) were added to 50 mL of carbon tetrachloride and the mixture was refluxed for 16 h. Reaction mixture was concentrated and purified by chromatography (0-30% EtOAc/hexanes) to give 1.8 g of the title compound along with small amount of unreacted starting material. 1H NMR (CDCl3, 200 MHz): δ=7.09 (d, 1H, J=3.4 Hz), 6.54 (d, 1H, J=3.6 Hz), 4.84 (s, 2H), 4.51 (q, 2H, J=7.0 Hz), 1.49 (t, 3H, J=7.4 Hz).

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. customReaction mixture
  3. concentrationwas concentrated
  4. custompurified by chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7c2a95aed20f47919f00211509cf9dda
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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