Potassium Iodide → 2-Bromo-9,10-diphenylanthracene

Participants

Reaction Conditions

Reaction Steps

About 7.6 g (17 mmol) of the obtained 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol, 5.1 g (31 mmol) of potassium iodide, 9.7 g (92 mmol) of sodium phosphinate monohydrate, and 50 mL of glacial acetic acid were put into a 500 mL three-neck flask, and the mixture was refluxed at 120° C. for two hours. Thereafter, 30 mL of 50% phosphinic acid was added to the reaction mixture, and the mixture was stirred at 120° C. for one hour. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extract was combined with an organic layer to be dried with magnesium sulfate. After the drying, this mixture was suction filtered, and the obtained filtrate was concentrated to give a solid substance. This solid substance was dissolved in toluene, and the solution was 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. The obtained filtrate was concentrated to give a solid substance, and the solid substance was recrystallized with a mixed solvent of chloroform and hexane, giving 5.1 g of 2-bromo-9,10-diphenylanthracene, which was the object of the synthesis, as a light yellow powdered solid substance. The yield of the two stages (ii) and (iii) was 74%.

Provenance & Evidence