Benzoyl Peroxide → HCID 86713387, compound

HRID 921268Notes

Reaction equation

HRID 921268 reaction equation
[CH3:1][O:2][N:3]([CH3:16])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[N+:12]([O-:14])=[O:13].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][CH2:11][C:7]1[C:6]([N+:12]([O-:14])=[O:13])=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([N:3]([O:2][CH3:1])[CH3:16])=[O:15]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 60644715HCID 60644715, compound

Product 1

HCID 86713387HCID 86713387, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Intermediate 37A (5.5 g, 24.53 mmol), NBS (5.24 g, 29.4 mmol) and benzoyl peroxide (0.594 g, 2.453 mmol) in CCl4 (80 mL) was purged with nitrogen and then heated to 80° C. for 4.5 h. The reaction mixture was cooled to room temperature and then quenched with water. The mixture was extracted with DCM and the combined extracts were washed with saturated NaHCO3 and brine and then dried (Na2SO4), filtered and concentrated to dryness. The crude material was purified by flash chromatography (SiO2, 80 g column, EtOAc/hexane=0-100%) to afford Intermediate 37B.

Workup

  1. customwas purged with nitrogen
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with water
  4. extractionThe mixture was extracted with DCM
  5. washthe combined extracts were washed with saturated NaHCO3 and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude material was purified by flash chromatography (SiO2, 80 g column, EtOAc/hexane=0-100%)

Sources & evidence

ORD record
ord-25f7e6f8790b473faeec4f40e0a3da04
Source dataset
uspto-grants-2016_03
Patent number
US09273014B2

Reaction notes

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