Carbon Tetrachloride → 3-(10-Bromoanthracen-9-yl)pyridine

Beteiligte Stoffe

Reaktionsschritte

In a 200 mL three-necked flask were placed 1.0 g (4.0 mmol) of 3-(9-anthryl)pyridine and 25 mL of carbon tetrachloride. Under a nitrogen stream, 10 mL of a carbon tetrachloride solution containing 0.83 g (5.1 mmol) of bromine was dripped into this solution, followed by stirring at room temperature for 26 hours. After a predetermined time has passed, 100 mL of a 1.0 M sodium thiosulfate solution was added to this mixture. The aqueous layer of this mixture was extracted with chloroform. The obtained extract and the organic layer were combined and washed with a saturated aqueous solution of sodium hydrogen carbonate and with saturated brine, and dried with magnesium sulfate. This mixture was subjected to gravity filtration, and the filtrate was concentrated to give a solid. A chloroform solution of the obtained solid was suction filtered 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. Recrystallization of this solid from a mixed solvent of ethyl acetate and hexane gave 0.74 g of a pale yellow powder in 53% yield, which was the desired substance.

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