Reaction #1543037

Reaction equation

5,11-dihydroindolo[3,2-b]carbazole

3-iodotoluene

potassium carbonate

n-tridecane

→

5,11-di-m-tolyl-5,11-dihydroindolo-[3,2-b]carbazole

5,11-di-m-tolyl-5,11-dihydroindolo[3,2-b]carbazole

Solvents

water

toluene

Conditions

Workup

1. 1
   OtherA 200-milliliter 3-necked round bottom flask equipped with a mechanical stirrer
2. 2
   Temperaturereflux condenser, and argon inlet
3. 3
   Otherwas purged with argon
4. 4
   TemperatureThe mixture was cooled to about 100° C.
5. 5
   OtherThe resulting two phase mixture was transferred into a separatory funnel
6. 6
   Otherthe layers separated
7. 7
   Washwas washed with water
8. 8
   workup.ADDITIONtreated with 25 grams of alumina under an argon atmosphere
9. 9
   Filtrationfiltered
10. 10
    OtherThe filtrate was then evaporated
11. 11
    Otherthe residue was recrystallized from cyclohexane

Procedure

A 200-milliliter 3-necked round bottom flask equipped with a mechanical stirrer, reflux condenser, and argon inlet was purged with argon and then charged with 5,11-dihydroindolo[3,2-b]carbazole (5.1 grams, 0.02 mol), 3-iodotoluene (8.69 grams, 0.04 mol), copper sulfate pentahydrate (0.25 gram, 1.0 mmol), potassium carbonate (5.52 grams, 0.04 mol), and n-tridecane (5.0 milliliters). Under an argon atmosphere, the reaction mixture was heated to about 250° C. with a heating mantle and allowed to proceed at this temperature to completion in about 6 hours. The mixture was cooled to about 100° C., and 100 milliliters of toluene and 15 milliliters of water were then added with vigorous stirring. The resulting two phase mixture was transferred into a separatory funnel and the layers separated. The organic phase, which contained the desired product, was washed with water, and treated with 25 grams of alumina under an argon atmosphere, and filtered. The filtrate was then evaporated and the residue was recrystallized from cyclohexane to provide 6.8 grams of pure, about 99.9 percent, 5,11-di-m-tolyl-5,11-dihydroindolo-[3,2-b]carbazole (1).

Source