3,4-Dichlorophenol → 2-(3,4-Dichlorophenoxy)-5-(ethylsulfonyl)pyridine

HRID 1758005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758005
CC([O-])(C)C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[CH:12][C:13]=1[Cl:14].C(S([C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH2:30][CH3:31])(=[O:29])=[O:28])=[CH:23][N:22]=1)(=O)=O)C>C1COCC1.CS(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[Cl:14])[O:15][C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH2:30][CH3:31])(=[O:28])=[O:29])=[CH:23][N:22]=1

Komponenten

6

Edukt 3

HCID 72583,4-DichlorophenolHCID 132780152,5-Bis(ethylsulfonyl)pyridineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 131027052-(3,4-Dichlorophenoxy)-5-(ethylsulfonyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 6.7 g of t-BuOK in a mixture of 50 ml of THF and 50 ml of DMSO was added 8.2 g of 3,4-dichlorophenol and then 7.9 g of 2,5-bis(ethylsulfonyl)pyridine, and the resulting mixture heated at 55° C. for 3 hrs. The reaction mixture was cooled and then poured into ice-water. A precipitate formed which was collected by filtration and then washed with water. The recovered solid was then dissolved in CH2Cl2 and dried over MgSO4. The solution was diluted with an equal volume of hexane and treated with silica gel and then filtered. The solution was then concentrated to 50 ml, cooled and 6.5 g of 2-(3,4-dichlorophenoxy)-5-ethylsulfonyl)pyridine recovered as a white powder, m.p. 117°-118° C.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customA precipitate formed which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. dissolutionThe recovered solid was then dissolved in CH2Cl2
  6. dry with materialdried over MgSO4
  7. additionThe solution was diluted with an equal volume of hexane
  8. additiontreated with silica gel
  9. filtrationfiltered
  10. concentrationThe solution was then concentrated to 50 ml
  11. temperaturecooled
  12. custom6.5 g of 2-(3,4-dichlorophenoxy)-5-ethylsulfonyl)pyridine recovered as a white powder, m.p. 117°-118° C.

Quellen und Nachweise

ORD-Eintrag
ord-6d43749f31324507b7834d7845047778
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04371537

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