Carbazole → 9-(p-Tolyl)carbazole

Participants

Reaction Steps

32.0 g (191 mmol) of carbazole, 50.0 g (229 mmol) of 4-iodotoluene, 2.02 g (31.9 mmol) of copper powder, 16.8 g (53.7 mmol) of 18-crown-6-ether and 29.0 g (210 mmol) of potassium carbonate were placed in a 500 ml four-necked flask with a mechanical stirrer and bulb-shaped cooler. To this was added 300 ml of o-dichlorobenzene as solvent. The resultant product was heated to 180° C. under a nitrogen flow in a silicone oil bath, and subjected to the reaction for 113 hours. After the reaction was completed, the reaction product was subjected to suction filtration with a suction funnel, before it was cooled down. The resultant filtrate was concentrated in an evaporator. To the resultant oily product was added 200 ml of methanol. The precipitated solid was subjected to the filtration at a reduced pressure with a suction funnel to obtain a gray solid, which was recrystallized in the presence of benzene to obtain 31.0 g of a white crystal.

Provenance & Evidence