Benzenesulfonyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a solution of 4-bromo-1H-indole (200 g) in tetrahydrofuran (2.0 L) was ice-cooled to 0° C., and sodium hydride (49 g) was added thereto, followed by stirring under ice-cooling for 1 hour. Benzenesulfonyl chloride (200 g) was added dropwise under ice-cooling to the reaction mixture, and the ice bath was removed, followed by stirring at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by ethyl acetate extraction. The organic layer was washed with brine and dried over magnesium sulfate, followed by filteration. The resulting residue was washed with isopropylether-hexane (1:1, 1.0 L), and then dried to obtain the title compound (310 g) having the following physical properties.

Provenance & Evidence