Реакция #347618

Уравнение реакции

hexafluoroacetone

n-BuLi

2,6-dibromopyridine

hexane

→

title compound

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

Растворители

THF

Условия реакции

Обработка

1. 1
   Другоеwas obtained (10 min)
2. 2
   Другоеprepared
3. 3
   Другоеby bubbling hexafluoroacetone into THF (10 mL) at -70° for 3 min
4. 4
   ДругоеThe resulting reaction mixture
5. 5
   workup.STIRRINGwas stirred for 15 min.
6. 6
   Другоеquenched with an aqueous solution of NH4Cl (8 mL)
7. 7
   Экстракцияwas extracted with Et2O
8. 8
   ДругоеAfter drying
9. 9
   Другоеevaporation of the organic extract
10. 10
    Другоеthe residue was chromatographed on silica gel with hexane
11. 11
    workup.DISTILLATIONEtOAc, followed by bulb-to-bulb distillation

Методика

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.

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