Benzoyl Peroxide → 4-(Bromomethyl)benzenesulfonyl chloride

HRID 910752Notes

Reaction equation

HRID 910752 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([Cl:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1.[Br:30]N1C(=O)CCC1=O>ClCC(Cl)C>[Br:30][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([Cl:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

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

Product 1

HCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 65641,2-DichloropropaneSolvent

Conditions

Temperature
80 °C

Procedure

At 20° C. benzoyl peroxide (600 mg) was added to a suspension of 4-methyl-benzenesulfonyl chloride (9.5 g) and N-bromosuccinimide (8.9 g) in 1,2-dichloropropane (60 ml). The reaction mixture was stirred at 80° C. for 2 h. The reaction mixture was concentrated and the title compound was obtained as a white solid after recrystallization from heptane. Yield: 2.26 g.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-aa14240b614f4c47a73dded39957c9aa
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

Loading…