Iodine → 2-Chloro-p-toluenesulfochloride

HRID 1440486Notes

Reaction equation

HRID 1440486 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([Cl:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.II.[Cl:14]Cl>[Fe](Cl)(Cl)Cl>[Cl:14][C:3]1[CH:4]=[C:5]([S:8]([Cl:11])(=[O:10])=[O:9])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 807IodineHCID 73974-Toluenesulfonyl chlorideHCID 24526Chlorine2×

Product 1

HCID 2597442-Chloro-p-toluenesulfochloride

Reagents, catalysts & solvents 1

HCID 24380Iron chloride (FeCl3)Catalyst

Procedure

576 g (3 mol) of 4-methylbenzenesulfonyl chloride are melted in a chlorination apparatus. After addition of 7 g of iron(III) chloride and 2 g of iodine, elemental chlorine is passed in (5 l Cl2 /h) at from 75° to 80° C. until 100% chlorination is achieved (GC analysis).

Sources & evidence

ORD record
ord-31918d95cdc34102be3d754968b08a44
Source dataset
uspto-grants-1996_03
Patent number
US05498798

Reaction notes

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