Hydrogen peroxide water → 5,6-Difluoropyridin-3-ol

HRID 873061

Reaktionsgleichung

Reaktionsgleichung von HRID 873061
[OH2:1].OO.[F:4][C:5]1[C:10]([F:11])=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][N:6]=1>O1CCCC1.O>[F:11][C:10]1[CH:9]=[C:8]([OH:1])[CH:7]=[N:6][C:5]=1[F:4]

Komponenten

5

Edukt 2

HCID 449047Hydrogen peroxide waterHCID 533983942,3-Difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Produkt 1

HCID 684308605,6-Difluoropyridin-3-olAusbeute 29,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of hydrogen peroxide water (1.50 mL, 13.2 mmol) and 2,3-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.8 g) in tetrahydrofuran (15 mL) was stirred at room temperature for 2 h, then diluted with water and extracted with ethyl acetate. Combined organic portions were washed with aqueous 5% sodium thiosulfate solution and saturated saline water, dried over anhydrous sodium sulfate and concentrated. Purification via Biotage Spla HPFC system (C18, mobile phase: 0.01% NH4HCO3, CH3CN/water, 10˜95%) afforded the title product as a white solid (450 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washCombined organic portions were washed with aqueous 5% sodium thiosulfate solution and saturated saline water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customPurification via Biotage Spla HPFC system (C18, mobile phase: 0.01% NH4HCO3, CH3CN/water, 10˜95%)

Quellen und Nachweise

ORD-Eintrag
ord-a29f2813bdc541dfb18fcf810d45f2e7
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975400B2

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