Reaktion #84793

Reaktionsgleichung

5-bromo-2,3-dimethoxybenzonitrile

2-furylboronic acid

dioxane

Na2CO3

→

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

Ausbeute 94.0%

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed
2. 2
   workup.WAITby alternately putting under house vacuum and argon three times for several minutes
3. 3
   TemperaturAfter cooling to room temperature
4. 4
   workup.ADDITIONthe mixture was diluted with H2O
5. 5
   Extraktionextracted with EtOAc
6. 6
   WaschenThe combined organics were washed with H2O and brine
7. 7
   Trocknendried over Na2SO4
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigePurification by chromatography (0-20% EtOAc-hexanes)

Vorschrift

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).

Quelle