Benzoyl Peroxide → HCID 21999886, compound

HRID 1975940Notes

Reaction equation

HRID 1975940 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:12][CH3:13])=[C:9]([CH3:11])[CH:10]=1)(=[O:4])=[O:3].C1C(=O)N([Br:21])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:12][CH3:13])=[C:9]([CH:10]=1)[CH2:11][Br:21])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21999877HCID 21999877, compound

Product 1

HCID 21999886HCID 21999886, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-methanesulfonyl-2-methoxytoluene (for preparation, see: U.S. Pat. No. 2,803,580 and Monatsh. Chem. 91, 57 (1960)) (298 mg), NBS (265 mg) and benzoylperoxide (catalytic amount) in CCl4 was irradiated with a sun lamp under reflux under a nitrogen atmosphere for 2 hours and cooled to room temperature. The solid was filtered off and the filtrate was concentrated and subjected to silica gel chromatogiraphy (hexanes/ethyl acetate 3:1) to give bromide 5 as a white solid.

Workup

  1. customfor preparation
  2. temperatureunder reflux under a nitrogen atmosphere for 2 hours
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-18d297fd738c414eb91e20c18d53c452
Source dataset
uspto-grants-2001_05
Patent number
US06225288B1

Reaction notes

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