Iodine → 2-Fluoro-3-iodo-5-methylpyridine

HRID 1912253

Reaktionsgleichung

Reaktionsgleichung von HRID 1912253
C([Li])CCC.C(NC(C)C)(C)C.[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=1.FC1C([Li])=CC(C)=CN=1.[I:30]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.O>[F:13][C:14]1[C:19]([I:30])=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=1

Komponenten

9

Edukt 6

HCID 807IodineHCID 7912DiisopropylamineHCID 24477Sodium ThiosulfateHCID 27746352-Fluoro-5-methylpyridineHCID 178418339ButyllithiumHCID 178506721HCID 178506721, Verbindung

Produkt 1

HCID 102432202-Fluoro-3-iodo-5-methylpyridineAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

26.5 ml of n-butyllithium (1.57 mol/l hexane solution) was dropwise added at −78° C. to a solution having 4.02 g (39.8 mmol) of diisopropylamine dissolved in 70 ml of tetrahydrofuran, followed by stirring for 30 minutes. To this solution, a solution having 4.42 g (39.8 mmol) of 2-fluoro-5-methylpyridine dissolved in 18 ml of tetrahydrofuran was added, followed by stirring for 4 hours to prepare 2-fluoro-5-methyl-3-pyridyllithium. Then, to this solution, a solution having 10.1 g (39.8 mmol) of iodine dissolved in 27 ml of tetrahydrofuran was added, followed by stirring for 2 hours. 16 ml of water and 120 ml of a sodium thiosulfate aqueous solution were charged, followed by extraction with ethyl ether. The organic layer was dried over magnesium sulfate and subjected to filtration, the solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel chromatography to obtain 3.15 g (yield: 33%) of 2-fluoro-3-iodo-5-methylpyridine.

Aufarbeitung

  1. additionwas added
  2. stirringby stirring for 4 hours
  3. additionwas added
  4. stirringby stirring for 2 hours
  5. extractionfollowed by extraction with ethyl ether
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationsubjected to filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe obtained crude product
  10. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-eabfac67f148444fa1aa0f62cc0b474c
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609150B2

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