Carbon Tetrachloride → 2-CHLORO-1-(p-CHLOROPHENYLSULFONYL)ETHYL p-t-BUTYLPHENYL SULFIDE

Reaction equation

[CH:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4])=[CH2:2].[C:13]([C:17]1[CH:22]=[CH:21][C:20]([S:23]Cl)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].C(Cl)(Cl)(Cl)[Cl:26]>>[C:13]([C:17]1[CH:18]=[CH:19][C:20]([S:23][CH:1]([S:3]([C:6]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=2)(=[O:4])=[O:5])[CH2:2][Cl:26])=[CH:21][CH:22]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

Reactant 3

HCID 5943Carbon Tetrachloride

HCID 217031-Chloro-4-(ethenylsulfonyl)benzene

HCID 12801136p-t-Butylbenzenesulfenyl chloride

Product 1

HCID 130448072-CHLORO-1-(p-CHLOROPHENYLSULFONYL)ETHYL p-t-BUTYLPHENYL SULFIDEYield 61%

Procedure

To a solution of 26.1 g (0.129 mole) of p-chlorophenyl vinyl sulfone in 100 ml of carbon tetrachloride at 25° C. was added 25.9 (0.129 mole) of p-t-butylbenzenesulfenyl chloride. The reaction mixture was allowed to stand for six days in a closed flask. Removal of the solvent by evaporation gave 55 g (106%) of crude product, m.p. 52°-68°. Recrystallization from 300 ml ethylacetatepentane (1:5) gave 31.5 g (61%) of pure product, m.p. 65°-67°.