Benzenesulfonyl chloride → 5-(Phenylmethoxy)-1-phenylsulfonylindole

Participants

Reaction Steps

4 M NaOH (100 mL, 0.4 mol) was added to a solution of 5-benzyloxyindole (20 g, 0.09 mol), tetrabutylammonium hydrogen sulfate (6.1 g, 0.018 mol) and benzenesulfonyl chloride (27 g, 0.15 mol) in DCM (500 mL) The mixture was stirred at room temperature for 6 hours and additional benzenesulfonyl chloride (4.1 g, 0.023 mol) was added. The mixture was stirred overnight and diluted with water and DCM. The mixture was transferred to a separation funnel and extracted with DCM (2×), dried (MgSO4) and evaporated. The crude product was suspended in diethylether (1000 mL) and filtered. The solid cake was washed with diethylether (2×) and discarded. The filtrate was evaporated to approximate 100 mL (precipitation of white solid) and filtered. The white crystals were washed with cold diethylether (2×) and dried in vacuo to give 15 g of a white solid. MS m/z 364 [M+H]+

Provenance & Evidence