反应详情

温度

65 °C

Into a 500 mL round bottom flask fitted with a mechanical stirrer, addition funnel, reflux condenser and nitrogen inlet were placed 12 g of sodium hydride (60% dispersion in mineral oil) and 30 mL of THF. Carbazole (33.4 g, 0.2 mole) was dissolved in 200 mL THF and the pale yellow solution was added dropwise to the reaction mixture while stirring and maintaining the temperature at 35˜40° C. Thereafter, 36.2 g (0.3 mole) of allyl bromide was added drop wise to the reaction mixture and stirring continued for an additional 15 minutes. Tetra-n-butyl ammonium bromide (1.3 g) was added followed by stirring for 20 minutes, and then the temperature was raised to 65° C. and kept at that temperature overnight. The reaction mixture was cooled to room temperature and after filtration, the solvent was removed using a rotary evaporator. The resulting yellow solid was twice recrystallized from methanol to give 34 g (81% yield) of colorless crystalline 9-allyl carbazole m.p. 53-54° C.

1. customInto a 500 mL round bottom flask fitted with a mechanical stirrer, addition funnel
2. temperaturereflux condenser and nitrogen inlet
3. additionthe pale yellow solution was added dropwise to the reaction mixture
4. temperaturemaintaining the temperature at 35˜40° C
5. stirringstirring
6. stirringby stirring for 20 minutes
7. customkept at that temperature overnight
8. temperatureThe reaction mixture was cooled to room temperature
9. filtrationafter filtration
10. customthe solvent was removed
11. customa rotary evaporator
12. customThe resulting yellow solid was twice recrystallized from methanol