Acetone → 2-(6-Bromo-3-pyridyl)-2-propanol

HRID 351744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351744
[Br:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.C([Li])CCC.[CH3:14][C:15]([CH3:17])=[O:16]>C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:15]([OH:16])([CH3:17])[CH3:14])=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

Produkt 1

HCID 223919732-(6-Bromo-3-pyridyl)-2-propanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 2,5-dibromopyridine in diethyl ether (5 mL/mmol) was cooled to −78° C., and n-butyllithium 2.5M in hexanes (1.05 eq) was added slowly. After 2 hrs in the cold, acetone (1.3 eq) was added and stirring was continued for 1 hour. The resulting mixture was quenched with saturated aqueous ammonium chloride solution, warmed to room temperature, and partitioned between ether and water. The crude product from the organic phase was triturated with 1:1 ether-hexane and filtered to afford the 2-bromo-5-(1-hydroxy-1-methylethyl)pyridine compound as a solid.

Aufarbeitung

  1. customThe resulting mixture was quenched with saturated aqueous ammonium chloride solution
  2. custompartitioned between ether and water
  3. customThe crude product from the organic phase was triturated with 1:1 ether-hexane
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-f86621b8f6b34087a7fb11081435292d
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743802B2

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