Sulfur dichloride → 2-CHLORO-1-(PHENYLSULFONYL)ETHYL p-t-BUTYLPHENYL SULFIDE

HRID 1156379Notes

Reaction equation

HRID 1156379 reaction equation
[CH:1]([S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])=[O:4])=[CH2:2].[C:12]([C:16]1[CH:21]=[CH:20][C:19]([S:22]Cl)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].S(Cl)[Cl:25]>C(Cl)(Cl)(Cl)Cl.C(O)(=O)C>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([S:22][CH:1]([S:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)(=[O:4])=[O:5])[CH2:2][Cl:25])=[CH:20][CH:21]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 25353Sulfur dichlorideHCID 79664Phenyl vinyl sulfoneHCID 12801136p-t-Butylbenzenesulfenyl chloride

Product 1

HCID 130448022-CHLORO-1-(PHENYLSULFONYL)ETHYL p-t-BUTYLPHENYL SULFIDEYield 52%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 25.2 g (0.150 mole) of phenyl vinyl sulfone in 100 ml of carbon tetrachloride and 30 ml of glacial acetic acid was treated with 30.1 g (0.150 mole) of p-t-butylbenzenesulfenyl chloride. There was an exotherm of 2° within 10 minutes. The red color of the sulfenyl chloride disappeared within 24 hours. Evaporation of the solvent left 54 g (98%) of crude product m.p. 58°-69°. Recrystallization from 100 ml of ethyl acetate-petroleum ether (1:1) gave 29 g (52%) of colorless crystals, m.p. 67°-69°.

Workup

  1. customan exotherm of 2°
  2. customwithin 10 minutes
  3. customEvaporation of the solvent
  4. waitleft 54 g (98%) of crude product m.p. 58°-69°
  5. customRecrystallization from 100 ml of ethyl acetate-petroleum ether (1:1)

Sources & evidence

ORD record
ord-c31442d7eb4c43d5abc99325f356301f
Source dataset
uspto-grants-1982_06
Patent number
US04335142

Reaction notes

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