Iodine → 2-Iodo-9,10-diphenylanthracene

Participants

Reaction Conditions

Reaction Steps

Into a 500 mL three neck flask was put 10 g (24 mmol) of 2-bromo-9,10-diphenylanthracene, and the atmosphere in the flask was substituted with nitrogen. Then, 150 mL of tetrahydrofuran was added thereto and dissolved well. This solution was stirred at −78° C. Then, 19 mL of n-butyllithium solution (1.6 mmol/L) was dropped into this solution using a syringe, stirred at −78° C. for one hour, and reacted to precipitate a white solid substance. After the reaction, a solution in which 12 g (49 mmol) of iodine was dissolved into 80 mL of tetrahydrofuran was dropped into the reaction mixture using a funnel for dropping. After the dropping, this mixture was stirred at −78° C. for one hour and then at room temperature for 12 hours. After the reaction, a sodium thiosulfate solution was added to the reaction solution, followed by stirring at room temperature for one hour. Ethyl acetate was added to this mixture, followed by extraction. An organic layer was separated from an aqueous layer and washed with an aqueous solution of sodium thiosulfate and then a saturated saline solution in this order. An organic layer was separated from an aqueous layer and dried with magnesium sulfate. This mixture was suction filtered so that the magnesium sulfate was removed. The obtained filtrate was concentrated to give a solid substance. Methanol was added to this solid substance, followed by washing with ultrasonic wave irradiation, whereby a solid substance was precipitated. This solid substance was collected by suction filtration to give 9.9 g of a light yellow powdered solid substance in 90% yield.

Provenance & Evidence