Reaktion #347618

Reaktionsgleichung

hexafluoroacetone

n-BuLi

2,6-dibromopyridine

hexane

→

title compound

2-Bromo-6-(hexafluoro-2-hydroxyprop-2-yl)pyridine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas obtained (10 min)
2. 2
   Sonstigeprepared
3. 3
   Sonstigeby bubbling hexafluoroacetone into THF (10 mL) at -70° for 3 min
4. 4
   SonstigeThe resulting reaction mixture
5. 5
   workup.STIRRINGwas stirred for 15 min.
6. 6
   Sonstigequenched with an aqueous solution of NH4Cl (8 mL)
7. 7
   Extraktionwas extracted with Et2O
8. 8
   SonstigeAfter drying
9. 9
   Sonstigeevaporation of the organic extract
10. 10
    Sonstigethe residue was chromatographed on silica gel with hexane
11. 11
    workup.DISTILLATIONEtOAc, followed by bulb-to-bulb distillation

Vorschrift

To a suspension of 2,6-dibromopyridine (2.37 g, 10 mmol) in THF (25 mL) at -70° there was added slowly n-BuLi, 1.4M, in hexane (7.9mL, 11 mmol). The resulting mixture was stirred in the cold until a solution was obtained (10 min). This solution was cannulated into a solution of hexafluoroacetone prepared by bubbling hexafluoroacetone into THF (10 mL) at -70° for 3 min. The resulting reaction mixture was stirred for 15 min., then quenched with an aqueous solution of NH4Cl (8 mL). The suspension was allowed to warm to r.t. and was extracted with Et2O. After drying and evaporation of the organic extract, the residue was chromatographed on silica gel with hexane:EtOAc, followed by bulb-to-bulb distillation to afford the title compound, m.p. 67°-69° C.

Quelle