반응 #84793

반응 방정식

5-bromo-2,3-dimethoxybenzonitrile

2-furylboronic acid

dioxane

Na2CO3

→

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

수율 94.0%

용매

H2O

반응 조건

후처리

1. 1
   기타The mixture was degassed
2. 2
   workup.WAITby alternately putting under house vacuum and argon three times for several minutes
3. 3
   온도After cooling to room temperature
4. 4
   workup.ADDITIONthe mixture was diluted with H2O
5. 5
   추출extracted with EtOAc
6. 6
   세척The combined organics were washed with H2O and brine
7. 7
   건조dried over Na2SO4
8. 8
   농축concentrated in vacuo
9. 9
   기타Purification by chromatography (0-20% EtOAc-hexanes)

실험 절차

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).

출처