Iodine → 2-Iodo-2',4',6'-triisopropyl-3-methoxybiphenyl

関与物質

反応手順

An oven-dried three-neck round bottom flask, which was equipped with a magnetic stir bar and charged with magnesium shavings (2.4 equiv), was fitted with a reflux condenser, glass stopper, and rubber septum. The flask was purged with argon and then THF (1 mL/mmol) and 2,4,6-triisopropylbromobenzene (2 equiv) were added via syringe. The reaction mixture was heated to reflux and 1,2-dibromethane (40 uL) was added via syringe. The reaction was allowed to stir at reflux for 1.5 h and was then cooled to room temperature. A separate oven-dried round bottom flask, which was equipped with a magnetic stir bar and fitted with a septum, was purged with argon and then THF (10 mL/mmol) and 3-fluoroanisole (1 equiv) were added to the flask via syringe. The reaction mixture was cooled to −78° C. and n-BuLi (1.05 equiv) was added in a dropwise fashion over a 40 min period. The solution was stirred for 1 h and the Grignard reagent, which was prepared in the first reaction vessel, was added via cannula over a 30 min period and allowed to stir at −78° C. for 1 h. The reaction mixture was warmed to room temperature slowly where it was stirred for an additional 12 h. The mixture was then cooled to 0° C. and a solution of Iodine in THF (1 M, 2 equiv) was added via syringe over a 15 min period and then the dark red solution was warmed to room temperature and stirred for 1 h. The solvent was removed via a rotary evaporator, and the remaining dark brown oil was taken up in Et2O, washed with a saturated solution of sodium sulfite, and washed with brine. The organic layer was then dried over MgSO4, filtered, and the solvent was removed via rotary evaporator to give a yellow solid. The crude material was recrystallized to give the desired product as a white solid.

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