Potassium Chloride → Benzene, 1,4-bis(phenylthio)-

HRID 1078704Notes

Reaction equation

HRID 1078704 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrBr.[Cl-].[K+]>ClCCl>[C:16]1([S:15][C:12]2[CH:13]=[CH:14][C:9]([S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:10][CH:11]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 4873Potassium ChlorideHCID 24408BromineHCID 18791838HCID 18791838, compound

Product 1

HCID 626321Benzene, 1,4-bis(phenylthio)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A 500-mL, round-bottom flask with a Teflon-covered magnetic stirring bar is charged with dichloromethane (50 mL), 10% KHCO3 (43 mL), and phenyl[4-(thiophenoxy)phenyl] sulfoxide (5 g, 17.0 mmol). To the reaction mixture is added bromine (2.72 g, 17.0 mmol) in dichloromethane (50 mL) over a period of 5 min with vigorous stirring. The reaction is continued for 30 min. To the reaction mixture is added a KCl saturated solution and dichloromethane (100 mL). The aqueous layer is extracted with dichloromethane (2×50 mL). The organic layer is washed with water, dried over anhydrous sodium sulfate, and filtered. After recrystallization from ether, the solid is obtained. The solid is dried under vacuum at room temperature for 20 h and then is used without further purification for polymerization.

Workup

  1. extractionThe aqueous layer is extracted with dichloromethane (2×50 mL)
  2. washThe organic layer is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customAfter recrystallization from ether
  6. customthe solid is obtained
  7. customThe solid is dried under vacuum at room temperature for 20 h
  8. customis used without further purification for polymerization

Sources & evidence

ORD record
ord-e40e783d14074e25945d5efa86c78a76
Source dataset
uspto-grants-1996_08
Patent number
US05550171

Reaction notes

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