Reacción #84793

Ecuación de reacción

5-bromo-2,3-dimethoxybenzonitrile

2-furylboronic acid

dioxane

Na2CO3

→

5-(furan-2-yl)-2,3-dimethoxybenzonitrile

Rendimiento 94.0%

Disolventes

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was degassed
2. 2
   workup.WAITby alternately putting under house vacuum and argon three times for several minutes
3. 3
   TemperaturaAfter cooling to room temperature
4. 4
   workup.ADDITIONthe mixture was diluted with H2O
5. 5
   Extracciónextracted with EtOAc
6. 6
   LavadoThe combined organics were washed with H2O and brine
7. 7
   Secadodried over Na2SO4
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   OtroPurification by chromatography (0-20% EtOAc-hexanes)

Procedimiento

To a mixture of 5-bromo-2,3-dimethoxybenzonitrile (0.958 g, 4.0 mmol), 2-furylboronic acid (0.53 g, 4.7 mmol), dioxane (24 mL), H2O (8 mL) and Na2CO3 (1.1 g, 10.4 mmol) was added tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol). The mixture was degassed by alternately putting under house vacuum and argon three times for several minutes each then heated at 85° C. under argon for 16.5 hrs. After cooling to room temperature, the mixture was diluted with H2O and extracted with EtOAc. The combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-20% EtOAc-hexanes) provided 5-(furan-2-yl)-2,3-dimethoxybenzonitrile as a white solid (0.85 g, 94% yield).

Fuente