Benzoyl Peroxide → 4-(Bromomethyl)benzenesulfonyl chloride

HRID 892825Notes

Reaction equation

HRID 892825 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([Cl:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:1]1[CH:2]=[CH:3][C:4]([S:7]([Cl:10])(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 73974-Toluenesulfonyl chlorideHCID 67184N-bromobutanimide

Product 1

HCID 27344094-(Bromomethyl)benzenesulfonyl chlorideYield 28.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

p-Toluenesulfonyl chloride (0.52 mol, 100 g), N-bromosuccinimide (0.62 mol, 110.3 g), and benzoyl peroxide (5 g) were heated to reflux in carbon tetrachloride (500 ml) for 1 hour. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was triturated with isopropyl ether to afford 40.1 g of title product as a white solid; m.p. 70°-73° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was triturated with isopropyl ether

Sources & evidence

ORD record
ord-6206c61a06b7448d9d60fa347417637d
Source dataset
uspto-grants-1992_06
Patent number
US05120754

Reaction notes

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