3'-(Trifluoromethylthio)acetophenone → HCID 59506285, Verbindung

HRID 1098756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1098756
[F:1][C:2]([S:5][C:6]1[CH:7]=[C:8]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][CH:11]=1)([F:4])[F:3].[OH:15]OS([O-])=O.[K+]>CO.C1COCC1.O>[F:1][C:2]([F:4])([F:3])[S:5]([C:6]1[CH:7]=[C:8]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][CH:11]=1)=[O:15]

Komponenten

6

Edukt 2

HCID 27778383'-(Trifluoromethylthio)acetophenoneHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 59506285HCID 59506285, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 1-(3-trifluoromethylsulfanyl-phenyl)ethanone (1.4 g, 6.36 mmol) in methanol (30 ml) and THF (30 ml) a solution of oxone, monopersulfate compound (10.94 g, 17.8 mmol) in water (50 ml) was added dropwise over a period of 10 min. The reaction mixture was stirred at 60° C. for 3 days. The organic solvent was removed in vacuo and the aqueous phase was extracted with dichloromethane. Evaporation of the combined organic layers and purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane gave the desired product (0.66 g, 44%). 1-(3-Trifluoromethanesulfonyl-phenyl)ethanone (190 mg, 12%) was obtained as a side product which was used for the synthesis of example 77.

Aufarbeitung

  1. customThe organic solvent was removed in vacuo
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. customEvaporation of the combined organic layers and purification of the crude product by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e032b30bfad946b0b2dd8cf22f063ac6
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143242B2

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