Potassium Carbonate → 3,5-Dichlorophenylsulfide

HRID 1907172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907172
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:10][C:11]1[CH:12]=[C:13]([SH:18])[CH:14]=[C:15]([Cl:17])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([S:18][C:13]2[CH:14]=[C:15]([Cl:17])[CH:16]=[C:11]([Cl:10])[CH:12]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 764241,3-Dichloro-5-iodobenzeneHCID 27360963,5-Dichlorobenzenethiol

Produkt 1

HCID 211871173,5-DichlorophenylsulfideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into a 300 ml three-necked glass flask equipped with a thermometer, a reflux condenser and a stirrer, 3,5-dichloroiodobenzene 22.6 g (82.8 mmol) and dimethylformamide 200 ml were added, and argon was passed through the solution for 2 hours and 15 minutes. Then, 3,5-dichlorothiophenol 14.8 g (82.6 mmol), potassium carbonate 22.8 g (165 mmol) and cuprous iodide 1.57 g (8.24 mmol) were added, which were reacted for 3 hours at 95 to 100° C. with stirring. After completion of the reaction, the reaction mixture was cooled down to room temperature and separated with the addition of water and hexane:ethyl acetate (1:1), and the organic layer obtained was dried with anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained concentrate was purified by recrystallization, simple silica-gel column chromatography (eluent; hexane) to obtain bis(3,5-dichlorophenyl)sulfide 25.4 g as white solid (isolation yield; 95%).

Aufarbeitung

  1. additionwere added
  2. customwhich were reacted for 3 hours at 95 to 100° C.
  3. customAfter completion of the reaction
  4. customseparated with the addition of water and hexane:ethyl acetate (1:1)
  5. customthe organic layer obtained
  6. dry with materialwas dried with anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. concentrationthe obtained concentrate
  10. customwas purified by recrystallization, simple silica-gel column chromatography (eluent; hexane)

Quellen und Nachweise

ORD-Eintrag
ord-24a721f90a3a4219a2776f669bd42c97
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08597799B2

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