Bromine → 3-(10-Bromoanthracen-9-yl)pyridine

Beteiligte Stoffe

Reaktionsschritte

In a 200 μL three-neck flask, 1.0 g (4.0 mmol) of 3-(9-anthryl)pyridine and 25 mL of carbon tetrachloride were placed. Then, 10 μL of a carbon tetrachloride solution containing 0.83 g (5.1 mmol) of bromine was dripped into the solution under nitrogen stream, and the solution was stirred for 26 hours at room temperature. After a certain period, 100 mL of a 1.0 M sodium thiosulfate solution was added into the mixture. Then, an aqueous layer of the mixture was extracted with chloroform. The obtained extracted solution and the organic layer were combined, washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried with magnesium sulfate. The mixture was gravity filtered, and the obtained filtrate was condensed to give a solid. A chloroform solution of the solid was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina, and the filtrate was condensed to give a solid. The solid was recrystallized with ethyl acetate/hexane, so that 0.74 g of target pale yellow powder was obtained in a yield of 53%.

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