Water → 3-(Trifluoromethyl)quinoline

HRID 2098036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098036
I[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F-:12].[K+].Cl[C:15]([F:21])([F:20])C(OC)=O.O>CN(C)C=O.C(OCC)(=O)C>[F:20][C:15]([F:21])([F:12])[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Komponenten

7

Edukt 4

HCID 962WaterHCID 73935Methyl chlorodifluoroacetateHCID 522689Potassium FluorideHCID 112538363-Iodoquinoline

Produkt 1

HCID 120251663-(Trifluoromethyl)quinolineAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-Iodoquinoline (13.65 g, 53.5 mmol), cuprous iodide (21.12, 111 mmol), potassium fluoride (7.11 g, 122 mmol), and methyl 2-chloro-2,2-difluoroacetate (23 ml, 216 mmol) in dimethylforamide (200 ml) was placed into a preheated oil bath at 120° C. After stirring for 6 h, the solution was diluted water and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was flash chromatographed with 99:1, 49:1, 24:1, 23:2, 9:1, and 4:1 hexane:ethyl acetate as the eluant to afford 3.89 g (37% yield) of 3-(trifluoromethyl)quinoline. Method [7] retention time 4.67 min by HPLC (M+198).

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed with 99:1, 49:1, 24:1, 23:2, 9:1, and 4:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-6e252b27cd3741be9e42c32dab721bad
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450363B2

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