Toluene → 1-Bromo-3-(1-phenylethenyl)benzene

関与物質

反応手順

To a solution of 3-bromobenzophenone (2.2 g, 8.5 mmol, 1 eq) in 20 mL of dry tetrahydrofuran at 0° C. under N2 atmosphere, was added a toluene solution of the Tebbe's reagent (17 mL of 0.5 M solution, 8.5 mmol, 1 eq.) and the mixture was allowed to warm to room temperature. The reaction mixture was examined after 20 min by TLC (cyclohexane/ethyl acetate 2%) which showed complete conversion to the desired product. Diethyl ether (50 mL) was added and some drops of NaOH 0.1 M aqueous solution was slowly added to quench the reaction. The mixture was dried over magnesium sulfate, passed through a pad of Celite and evaporated. The solid formed was triturated with cyclohexane and filtered; the solution was collected and concentrated under reduced pressure. The crude was purified by flash chromatography eluting with cyclohexane. 2.02 g of clean product was obtained as colorless liquid (yield: 91%).

情報源と証拠