1,4-Dibromobenzene → 9-(4-Bromophenyl)carbazole

Participants

Reaction Conditions

Reaction Steps

In a 300 mL three-neck flask were put 56 g (240 mmol) of 1,4-dibromobenzene, 31 g (180 mmol) of 9H-carabazole, 4.6 g (24 mmol) of copper(I) iodide, 2.1 g (8.0 mmol) of 18-crown-6-ether, 66 g (480 mmol) of potassium carbonate, and 8 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (abbreviation: DMPU). This mixture was stirred under a nitrogen stream at 180° C. for 6 hours. After that, this mixture was filtered. The resulting filtrate was washed with dilute hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine in that order. The organic layer was dried with magnesium sulfate. This mixture was filtered. The resulting filtrate was concentrated to give a compound, which was then purified by silica gel column chromatography (the developing solvent was a mixed solvent of a 9:1 ratio of hexane to ethyl acetate). The fraction obtained was concentrated to give a compound. This compound was recrystallized with a mixed solvent of chloroform and hexane to give the desired substance as 21 g of a light brown plate-like crystal in a yield of 35%.

Provenance & Evidence