Sodium Carbonate → 2-Bromo-6-phenylpyridine

HRID 399704

Reaktionsgleichung

Reaktionsgleichung von HRID 399704
[C:1]1([C:7]2[NH:12][C:11](=O)[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)([Br:16])=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[Br:16][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:12]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 24613Phosphorus oxybromideHCID 878896-Phenyl-2-pyridone

Produkt 1

HCID 5686792-Bromo-6-phenylpyridineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 6-phenyl pyridone (3 g, 17.5 mmol; prepared according to Example 6) and phosphoryl bromide (7.2 g, 25.0 mmol) is heated to 100° C. for 5 h. The cooled mixture is poured into water (40 ml) and the pH is adjusted to 9 by addition of saturated aqueous sodium carbonate. Then the layers are separated and the aqueous layer is extracted with ethyl acetate (50 ml). The combined organic layers are dried with anhydrous magnesium sulphate and the solvent is evaporated in vacuo. The crude product is crystallized from aqueous ethanol. Subsequent purification by flash chromatography (silica gel, hexane/ethyl acetate 9/1 v/v) gives 2-bromo-6-phenyl pyridine (3.1 g, 76% of th.) as light brown crystals with mp 50° C.

Aufarbeitung

  1. customThen the layers are separated
  2. extractionthe aqueous layer is extracted with ethyl acetate (50 ml)
  3. dry with materialThe combined organic layers are dried with anhydrous magnesium sulphate
  4. customthe solvent is evaporated in vacuo
  5. customThe crude product is crystallized from aqueous ethanol
  6. customSubsequent purification by flash chromatography (silica gel, hexane/ethyl acetate 9/1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-54bf8adb3e9a4cfea711c2f3aa0cd14b
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05824624

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