Chlorobenzene → 4-Chlorobenzenesulfonyl chloride

HRID 846300Notes

Reaction equation

HRID 846300 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][S:9](O)(=[O:11])=[O:10].S(Cl)(Cl)=O>S(=O)(=O)(O)N.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:9]([Cl:8])(=[O:11])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7964ChlorobenzeneHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acid

Product 1

HCID 73984-Chlorobenzenesulfonyl chlorideYield 108.2%

Reagents, catalysts & solvents 2

HCID 5987Sulfamic AcidCatalystHCID 962WaterSolvent

Procedure

112.6 g (1.0 mol) of chlorobenzene are added dropwise at 70° C. over a period of 1 hour to 122 g (1.05 mol) of chlorosulfonic acid. The mixture is then stirred at this temperature for 15 minutes. 1 g of sulfamic acid is then added and 180 g (1.5 mol) of thionyl chloride are added dropwise at 70° C. in the course of 2 hours. Working up is carried out as described in Example 1. 228.3 g of moist 4-chlorobenzenesulfonyl chloride having a water content of 12% are obtained. This corresponds to 200.9 g of 4chlorobenzenesulfonyl chloride (94.4% of theory), calculated as dry material, having a purity of 95%.

Sources & evidence

ORD record
ord-bedf60d46cc94424ad37df6f84cb0b69
Source dataset
uspto-grants-1992_08
Patent number
US05136043

Reaction notes

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