Benzoyl Peroxide → HCID 59814418, compound

HRID 1514038Notes

Reaction equation

HRID 1514038 reaction equation
[C:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:22]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([CH2:21][Br:22])=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 86629954HCID 86629954, compound

Product 1

HCID 59814418HCID 59814418, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of N-Boc 3-Methylcarbazole (85 mg, 0.3 mmol) and N-bromo succinimide (54 mg, 0.3 mmol) in carbon tetrachloride (10 mL) was added benzoyl peroxide (10 mg), and the reaction was heated at reflux for about 12 h. The cooled reaction mixture was filtered through celite, the solvent was removed under reduced pressure and the crude product was purified using column chromatography on silica gel with hexane/ethyl acetate as eluant (86 mg, 80% yield). ES-MS (M-Br)+ 280.9 (calc. 280.15).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for about 12 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered through celite
  5. customthe solvent was removed under reduced pressure
  6. customthe crude product was purified

Sources & evidence

ORD record
ord-0a84a2cad61c4636a311aad236e34d48
Source dataset
uspto-grants-2012_07
Patent number
US08222215B2

Reaction notes

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