Benzoyl Peroxide → 1035263-40-1

HRID 1868943Notes

Reaction equation

HRID 1868943 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[I:9].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[I:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1384143-Chloro-2-iodotoluene

Product 1

HCID 670998331035263-40-1Yield 71.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-chloro-2-iodo-3-methylbenzene (7.5 g, 30 mmol) in 60 mL CCl4 stirred at 70° C. was treated with 1-bromopyrrolidine-2,5-dione (7.9 g, 45 mmol) and dibenzoyl peroxide (0.72 g, 3.0 mmol) slowly. The mixture was refluxed under a sunlight lamp for 15 hours. The mixture was cooled to room temperature, filtered through a plug of Celite, and rinsed with 10% EtOAc/hexane. The filtrate was concentrated and purified by column chromatography (0-10% EtOAc/hexane) to give 7.1 g pink oil.

Workup

  1. temperatureThe mixture was refluxed under a sunlight lamp for 15 hours
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through a plug of Celite
  4. washrinsed with 10% EtOAc/hexane
  5. concentrationThe filtrate was concentrated
  6. custompurified by column chromatography (0-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-9d23177617fb43beaecd7950b1cc48a6
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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