Dichloromethane → 2-CHLORO-1-(p-t-BUTYLPHENYLSULFONYL)ETHYL PHENYL SULFIDE

HRID 1156383Notes

Reaction equation

HRID 1156383 reaction equation
[CH:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4])=[CH2:2].[C:16]1([S:22]Cl)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(Cl)[Cl:25]>>[C:16]1([S:22][CH:1]([S:3]([C:6]2[CH:11]=[CH:10][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=2)(=[O:5])=[O:4])[CH2:2][Cl:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 8793221-Tert-butyl-4-(ethenesulfonyl)benzeneHCID 11008040Benzenesulfenyl chloride

Product 1

HCID 130448082-CHLORO-1-(p-t-BUTYLPHENYLSULFONYL)ETHYL PHENYL SULFIDEYield 86%

Procedure

To a solution of 21.0 g (93.7 moles) of p-t-butylphenyl vinyl sulfone in 100 ml of methylene chloride at 20° C. was added 14.0 ml (17,5 g, 121 mmoles) of benzenesulfenyl chloride. After 75 minutes the initial red color of the solution had changed to orange. In the same time the temperature of the solution rose to 26° C. After three days at 23° C. the solvent was removed by evaporation. The semicrystalline residue was recrystallized from ethyl acetate-pentane (1:2) to give a first crop of 18.3 g (53%), m.p. 104.0°-105.5° C. and subsequent crops of 8.3 and 3.0 g, for a total yield of 86%.

Workup

  1. customrose to 26° C
  2. customAfter three days at 23° C. the solvent was removed by evaporation
  3. customThe semicrystalline residue was recrystallized from ethyl acetate-pentane (1:2)
  4. customto give a first crop of 18.3 g (53%), m.p. 104.0°-105.5° C. and subsequent crops of 8.3 and 3.0 g

Sources & evidence

ORD record
ord-1811a6e43aa7448284219a9a5057e657
Source dataset
uspto-grants-1982_06
Patent number
US04335142

Reaction notes

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