反应详情

Into a 200-mL three-neck flask were put 1.6 g (6.1 mmol) of 2-chlorodibenzo[f,h]quinoxaline, 2.5 g (6.1 mmol) of 4,4′-bidibenzothiophene-6-boronic acid, and 0.19 g (0.62 mmol) of tris(2-methylphosphine)phosphine, and the air in the flask was replaced with nitrogen. To this mixture were added 20 mL of toluene, 10 mL of ethanol, and 6.0 mL of an aqueous solution of potassium carbonate (2.0 mol/L). This mixture was degassed by being stirred while the pressure was reduced. To this mixture, 70 mg (0.31 mmol) of palladium(II) acetate was added. This mixture was stirred at 80° C. under a nitrogen stream for 6 hours to precipitate a solid. The precipitated solid was collected by suction filtration. The collected solid was dissolved in approximately 6.0 L of hot toluene, and this solution was suction-filtered through Celite, alumina, and Florisil. The resulting filtrate was concentrated to give a solid. The solid was recrystallized by HPLC to give a white solid. The obtained solid was washed with hot toluene to give 1.5 g of white powder, which was an objective substance, in 41% yield. Synthesis Scheme (b-3) of Step 3 is shown below.

1. customInto a 200-mL three-neck flask were put
2. customThis mixture was degassed
3. stirringThis mixture was stirred at 80° C. under a nitrogen stream for 6 hours
4. customto precipitate a solid
5. filtrationThe precipitated solid was collected by suction filtration
6. dissolutionThe collected solid was dissolved in approximately 6.0 L of hot toluene
7. filtrationthis solution was suction-filtered through Celite, alumina, and Florisil
8. concentrationThe resulting filtrate was concentrated
9. customto give a solid
10. customThe solid was recrystallized by HPLC
11. customto give a white solid
12. washThe obtained solid was washed with hot toluene