Carbazole → 9-(4-Bromophenyl)carbazole

Participants

Reaction Conditions

Reaction Steps

56 g (240 mmol) of p-dibromobenzene, 31 g (180 mmol) of carbazole, 4.6 g (24 mmol) of copper iodide, 66 g (480 mmol) of potassium carbonate, and 2.1 g (8 mmol) of 18-crown-6-ether were put into a 300 mL three-necked flask, and nitrogen was substituted for the content of the flask. Then, 8 mL of N—N′-dimetylpropyleneurea was added thereto, and this mixture was stirred for 6 hours at 180° C. to be reacted. After the reaction, cooling of the reaction mixture to the room temperature was performed, and the precipitated object was removed by suction filtration. The filtrate was washed with dilute hydrochloric acid, a saturated sodium hydrogen carbonate solution, and a saturated saline solution, in this order, and then dried with magnesium sulfate. After drying, filtration was performed, and an oily substance that was obtained by concentrating the filtrate was purified by silica column chromatography. For the column purification, a mixed solvent of hexane:ethyl acetate=9:1 was used as a developing solvent. After the column purification, an obtained solution was re-crystallized with chloroform and hexane, whereby 21 g of a light brown solid of 9-(4-bromophenyl)carbazole was obtained in the yield of 35% (Synthesis Scheme (k-1)).

Provenance & Evidence