Phenol → 2-Bromo-6-phenoxypyridine

HRID 2080053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080053
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC(C)([O-])C.[K+].C(OCC)(=O)C>CS(C)=O.O>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Komponenten

7

Edukt 4

HCID 996PhenolHCID 8857Ethyl AcetateHCID 122742,6-DibromopyridineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 8245892-Bromo-6-phenoxypyridineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a solution of 2,6dibromopyridine (20 g, 84.4 mmol) and phenol (7.94 g, 84.4 mmol) in dimethylsulfoxide (200 mL) was added potassium tert-butoxide (9.47 g, 84.4 mmol), and the solution was stirred at 160° C. for 7 hours. The reaction solution was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), and 2-bromo-6-phenoxy-pyridine (19.6, 93%) was obtained as a yellow solid.

Aufarbeitung

  1. customwas allowed to room temperature
  2. customfor partitioning
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-4d8ded05359f457884c6ce9594307d28
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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