Chloroform → 2-Methylthio-2,2,2',4'-tetrafluoroacetophenone

HRID 1586436

Reaktionsgleichung

Reaktionsgleichung von HRID 1586436
[CH3:1][S:2][CH:3]([F:14])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])=[O:5].[F:15][N+]1C=CC(C)=CC=1S([O-])(=O)=O.CCCCCC.C(Cl)(Cl)Cl>ClC(Cl)CCl>[CH3:1][S:2][C:3]([F:15])([F:14])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])=[O:5]

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 8058HexaneHCID 2737404N-Fluoro-4-methylpyridinium-2-sulfonateHCID 106327011-(2,4-Difluorophenyl)-2-fluoro-2-(methylsulfanyl)ethanone

Produkt 1

HCID 102203472-Methylthio-2,2,2',4'-tetrafluoroacetophenoneAusbeute 47,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 65741,1,2-TrichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a 20 ml solution of 0.5 g (2.3 mmol) of 2-methylthio-2,2',4'-trifluoroacetophenone [Compound (2b-1)] in 1,1,2-trichloroethane, 0.7 g (3.7 mmol) of N-fluoro-4-methylpyridinium-2-sulfonate ("MEC-02", trade name; Daikin Industries, Ltd.) was added at an internal temperature of 80° C., followed by stirring at an internal temperature of 100° C. for 20 minutes. After cooling, the reaction mixture was added to n-hexane. The insoluble matter so precipitated was filtered off. The insoluble matter was then washed with ethyl ether, followed by combination with the hexane layer. The layers so combined were washed successively with water and saturated saline, followed by drying over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column using chloroform, whereby 0.26 g of the title Compound (2c-1) was obtained in the form of a light yellow oil (yield: 48.1%).

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe insoluble matter so precipitated
  3. filtrationwas filtered off
  4. washThe insoluble matter was then washed with ethyl ether
  5. washThe layers so combined were washed successively with water and saturated saline
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customThe residue so obtained

Quellen und Nachweise

ORD-Eintrag
ord-d6b8731c671a4d33a553d33cbf793a75
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05945438

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