Chloroselenobenzene → HCID 11012861, compound

Participants

Reaction Steps

Lithium diisopropylamide (2M solution in heptane/tetrahydrofuran/ethylbenzene) solution (11.98 mL) was added dropwise slowly to a solution of the compound 11 (6.58 g) in tetrahydrofuran (15 mL) and the solution was stirred at 30 minutes. A solution of Benzeneselenenyl chloride (4.59 g) in tetrahydrofuran (30 mL) was added dropwise slowly to the reaction solution, which was stirred at −78° C. for 1 hour. To the reaction solution was added an aqueous saturated ammonium chloride solution at −78° C. The reaction solution was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The reaction solution was filtrated through Celite (Brand name) and concentrated. The obtained residue was purified by flush column chromatography (n-hexane:ethyl acetate=20:1). To a solution of the obtained compound (3.87 g) in tetrahydrofuran/ethyl acetate (2:3) (80 mL) were added sodium bicarbonate (1.68 g) and 30% hydrogen peroxide solution (3.2 mL) at 0° C. After 1 hour, to the reaction mixture was added water. The reaction solution was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine, and dried over anhydrous magnesium sulfate. The reaction solution was filtrated through Celite (Brand name) and concentrated. The obtained residue was purified by flush column chromatography (n-hexane:ethyl acetate=15:1) to give the title compound (1.89 g) having the following physical data.

Provenance & Evidence