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General procedure: Aryl bromide (10 mmol) was dissolved in dry THF (30 mL) and cooled to -78 C under anargon atmosphere. n-Butyllithium (1.6 M in n-hexane; 7.5 mL; 12 mmol) was addeddropwise. After 15 minutes a solution of I2 (3.81 g; 15 mmol) in dry THF (10 mL) was addedand the reaction mixture was allowed to warm to room temperature overnight.For workup the reaction mixture was concentrated in vacuo. H2O was added to the residueand it was extracted with DCM (3x). The combined organic phases were washed withsaturated Na2S2O5 solution and H2O. After drying over MgSO4 and concentration underreduced pressure, the crude product was purified by column chromatography.
With iodine; magnesium; In tetrahydrofuran; at -10 - 50℃; for 5h;
A small amount of iodine (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added to 14 g of magnesium having a shaved form (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 230 ml of THF which was dried and distilled while heating at 50C and stirring to activate magnesium, and then a solution prepared by dissolving 129 g of 9-bromophenanthrene (manufactured by Tokyo Kasei Kogyo Co., Ltd.) in one liter of THF which was dried and distilled was dropwise added thereto in one hour. After finishing dropwise adding, the solution was stirred at 50C for 2 hours and cooled down to - 10C, and then 250 g of iodine was added little by little. The temperature was returned to a room temperature, and then stirring was continued for 2 hours. Water 100 ml was added to the above reaction liquid, and it was extracted with ethyl acetate. The ethyl acetate layer was extracted with a caustic soda aqueous solution, and after the aqueous layer was washed with hexane, it was acidified with hydrochloric acid and then extracted with ethyl acetate. After the extract was concentrated under reduced pressure, the resulting viscous liquid was dissolved again in a caustic soda aqueous solution and precipitated with an acid to obtain 91 g of 9-iodophenanthrene.
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