Hydrochloric Acid → 6-Fluoro-4-iodopyridin-3-ol

HRID 1640891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640891
Cl.[F:2][C:3]1[CH:8]=[C:7]([I:9])[C:6]([O:10]COC)=[CH:5][N:4]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[F:2][C:3]1[N:4]=[CH:5][C:6]([OH:10])=[C:7]([I:9])[CH:8]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 667381532-Fluoro-4-iodo-5-(methoxymethoxy)pyridine

Produkt 1

HCID 666745926-Fluoro-4-iodopyridin-3-olAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Add HCl (3 M in water, 31 mL, 93.0 mmol) to a solution of 2-fluoro-4-iodo-5-methoxymethoxy-pyridine (3.9 g, 13.8 mmol) in THF (20 mL). Stir the mixture at 60° C. for 3 h and cool down the mixture. Adjust the pH to 7 with slow addition of a saturated aqueous sodium bicarbonate solution. Extract the solution with ethyl acetate three times. Wash the organic layer with aqueous saturated sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to afford the title compound (3.2 g, 97%) as a yellow solid. MS (ES) m/z 240 [M+1]+.

Aufarbeitung

  1. temperaturecool down the mixture
  2. extractionExtract the solution with ethyl acetate three times
  3. washWash the organic layer with aqueous saturated sodium chloride
  4. dry with materialDry the mixture over sodium sulfate
  5. concentrationConcentrate the solution in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6078fe2da4e44b22bdb7af9e4042e7f6
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114872B2

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