Acetic Acid → 5-Bromo-2-fluoropyridin-3-ol

HRID 1685411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685411
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[C:5]([F:8])=[N:6][CH:7]=1.C(O)(=[O:14])C.C(OCC)(=O)C.OO>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([OH:14])[C:5]([F:8])=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 27832425-Bromo-2-fluoropyridine-3-boronic Acid (contains varying amounts of Anhydride)

Produkt 1

HCID 201118655-Bromo-2-fluoropyridin-3-olAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

A solution of 1.36 g (6.18 mM) of 5-bromo-2-fluoro-3-pyridineboronic acid in a mixture of 9.5 ml of ethanol, 2.3 ml of acetic acid and 1.3 ml of ethyl acetate is prepared. 2.2 ml of 30% hydrogen peroxide are added to the solution. The reaction mixture is stirred at a temperature of 35° C. for 3 hours and then cooled and extracted with ethyl ether. The organic phases are washed with a solution of ferrous ammonium sulfate, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The solid residue is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (9/1; v/v) as the eluent to give the desired product in the form of a white solid with a yield of 62%.

Aufarbeitung

  1. customis prepared
  2. temperaturecooled
  3. extractionextracted with ethyl ether
  4. washThe organic phases are washed with a solution of ferrous ammonium sulfate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe solid residue is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (9/1; v/v) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-240c76788df04d8cb985f26908ccdd5a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148407B2

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