Benzoyl Peroxide → HCID 68614659, compound

HRID 2189140Notes

Reaction equation

HRID 2189140 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Cl:9])=[CH:4][C:3]=1[CH3:10].[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Cl:9])=[CH:4][C:3]=1[CH2:10][Br:11]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 547587261-Bromo-4-chloro-5-fluoro-2-methylbenzene

Product 1

HCID 68614659HCID 68614659, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 75 mmol of 1-bromo-4-chloro-5-fluoro-2-methyl-benzene, 75 mmol of 1-bromo-pyrrolidine-2,5-dione and 0.74 mmol of benzoyl peroxide in 100 ml of carbon tetrachloride is heated to reflux for 15 hours. After evaporation of the solvent, the residue is partitioned between water and ethyl acetate. The organic layer is washed with water, and then with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title compound which is identified based on the Rf value.

Workup

  1. temperatureto reflux for 15 hours
  2. customAfter evaporation of the solvent
  3. customthe residue is partitioned between water and ethyl acetate
  4. washThe organic layer is washed with water
  5. dry with materialwith brine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-643849432d1345bdac683ff31d09817b
Source dataset
uspto-grants-2012_12
Patent number
US08324235B2

Reaction notes

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