Cesium carbonate → 4-(2-Methoxycarbonylphenyl)thio-2,3,5,6-tetrafluoropyridine

HRID 324990

Reaktionsgleichung

Reaktionsgleichung von HRID 324990
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[F:12][C:13]1[N:18]=[C:17]([F:19])[C:16]([F:20])=[C:15](F)[C:14]=1[F:22].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:11][O:10][C:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[S:4][C:15]1[C:14]([F:22])=[C:13]([F:12])[N:18]=[C:17]([F:19])[C:16]=1[F:20])=[O:9]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 14797Potassium HydroxideHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 69690Pentafluoropyridine

Produkt 1

HCID 154534494-(2-Methoxycarbonylphenyl)thio-2,3,5,6-tetrafluoropyridineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of methyl thiosalicylate (1.0 g, 5.9 mmol) in dry DMF (15 mL) at 0° C. was added pentafluoropyridine (1.2 g, 7.1 mmol) and cesium carbonate (2.5 g, 7.7 mmol). The resultant mixture was stirred at ambient temperature for 5 hours then poured into 100 mL of 0.5 M aqueous KOH solution and 100 mL of ethyl acetate. The aqueous layer was separated and extracted with another 100 mL of ethyl acetate. The combined organic extracts were washed with 0.5 M aqueous KOH solution (100 mL) then brine (100 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford 1.8 g (98% yield) of 4-(2-methoxycarbonylphenyl)thio-2,3,5,6-tetrafluoropyridine as a crystalline solid, NMR (CDCl3) 8.1 (dd, 1), 7.4 (m, 1), 7.4 (tt, 1), 7.0 (d, 1), 4.0 (s, 3) ppm.

Aufarbeitung

  1. customThe aqueous layer was separated
  2. extractionextracted with another 100 mL of ethyl acetate
  3. washThe combined organic extracts were washed with 0.5 M aqueous KOH solution (100 mL)
  4. dry with materialbrine (100 mL), dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fb92d67bfa0f4e128b25f65768ec81a5
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06221886B1

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