Benzoyl Peroxide → 3-(Bromomethyl)benzene-1-sulfonyl chloride

HRID 865934Notes

Reaction equation

HRID 865934 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]1([CH3:19])[CH:14]=[CH:13][CH:12]=[C:11]([S:15]([Cl:18])(=[O:17])=[O:16])[CH:10]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:19][C:9]1[CH:10]=[C:11]([S:15]([Cl:18])(=[O:16])=[O:17])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27345953-Methylbenzenesulphonyl chloride

Product 1

HCID 234473893-(Bromomethyl)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (6.27 g, 0.035 mole), m-toluenesulfonyl chloride (6.72 g, 0.035 mole), and benzoyl peroxide (0.67 g, 0.0019 mole) were combined in CCl4 (40 mL) and heated at reflux 2 h. The reaction mixture was filtered and washed with CCl4. The filtrate was concentrated to give m-bromomethylbenzenesulfonyl chloride, 9.74 g, as a viscous yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux 2 h
  3. filtrationThe reaction mixture was filtered
  4. washwashed with CCl4
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-00c80fcad393444eb335e6d9d03444a8
Source dataset
uspto-grants-1996_10
Patent number
US05569659

Reaction notes

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