Reacción #9350

Ecuación de reacción

N-bromosuccinimide

Lithium bis (trimethylsilyl) amide

Ethyl 3-pyridylacetate

Chlorotrimethylsilane

→

ethyl 2-bromo-2(3-pyridyl)acetate

Disolventes

H2O

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred for 20 minutes
2. 2
   workup.STIRRINGto stir
3. 3
   Temperaturawarm to room temperature overnight
4. 4
   ExtracciónThe organic layer was extracted with ethyl acetate
5. 5
   SecadoThe organic phase was dried over sodium sulfate
6. 6
   Otrothe solvent was evaporated
7. 7
   Otroto give a yellow oil
8. 8
   OtroThe resulting oil was chromatographed on silica gel

Procedimiento

Ethyl 3-pyridylacetate (1.0 g, 1.0 eq) was dissolved in THF (50 mL) and cooled to −78° C. Lithium bis (trimethylsilyl) amide (6.66 mL, 1.1 eq) was added to the reaction and stirred for 20 minutes. Chlorotrimethylsilane (1.44 mL, 1.875 eq) was added at −78° C. and stirred for 20 minutes. N-bromosuccinimide (1.09 g, 1.01 eq) was added to the reaction mixture. The reaction mixture was allowed to stir and warm to room temperature overnight. The reaction mixture was diluted with H2O. The organic layer was extracted with ethyl acetate. The organic phase was dried over sodium sulfate and the solvent was evaporated to give a yellow oil. The resulting oil was chromatographed on silica gel using hexanes and ethyl acetate (1:1) to give ethyl 2-bromo-2(3-pyridyl)acetate.

Fuente