Benzoyl Peroxide → HCID 57800477, compound

HRID 2102202Notes

Reaction equation

HRID 2102202 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)=[N:4][CH:3]=1.C1C(=O)N([Br:24])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:24][CH2:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:8]=2)=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 11436092HCID 11436092, compound

Product 1

HCID 57800477HCID 57800477, compoundYield 56.4%

Procedure

To a solution of 5-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-oxazole (Example 370B) (1.0 g, 4.4 mmol) was added NBS (0.784 g, 4.4 mmol) and benzoyl peroxide (0.100 g, 0.41 mmol). The mixture was refluxed for 1 h and the solids were filtered. The filtrate was concentrated and purified by radial chromatography (0-20% EtOAc-hexanes gradient) to afford the title compound (0.760 g, 56% yield): MS (ES) m/z 306 (M+1) and 308 (M+1, isotope).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. filtrationthe solids were filtered
  3. concentrationThe filtrate was concentrated
  4. custompurified by radial chromatography (0-20% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-152c5f052bb64a289e731518bb0f5679
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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