Mesitylene → 7-(4-Bromophenyl)-7H-dibenzo[c,g]carbazole

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Reaction Steps

In a 200 mL three-neck flask were placed 5.0 g (18 mmol) of 7H-dibenzo[c,g]carbazole, 13 g (47 mol) of 4-bromoiodobenzene, and 1.9 g (20 mmol) of sodium tert-butoxide. After the air in the flask was replaced with nitrogen, to this mixture were added 100 mL of mesitylene and 0.90 mL of tri-(tert-butyl)phosphine (a 10 wt % hexane solution). This mixture was degassed by being stirred while the pressure was reduced. After the degassing, 0.51 g (0.90 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred at 170° C. for 17 hours under a nitrogen stream. After the stirring, 20 mL of water was added to the obtained mixture. The aqueous layer of this mixture was extracted with toluene, and the solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate, and this mixture was gravity-filtered. A solid obtained by concentration of the obtained filtrate was dissolved in about 30 mL of toluene. This solution was suction-filtered through Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). A solid obtained by concentration of the filtrate was recrystallized from toluene/hexane to give 2.9 g of pale yellow needle-like crystals, which was the object of the synthesis, in a yield of 38% yield. A reaction scheme (c-2) of Step 3 is illustrated below.

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