Benzoyl Peroxide → 3-(Bromomethyl)benzene-1-sulfonyl chloride
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureheated
- temperatureat reflux 2 h
- filtrationThe reaction mixture was filtered
- washwashed with CCl4
- 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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