Phosphorus oxychloride → 3-(chloromethyl)-1-tosyl-1H-indole

Participants

Reaction Steps

To a solution of (1-tosyl-1H-indol-3-yl)methanol (1.0 g, 3.318 mmol) in dry THF (10 mL), POCl3 (0.661 g, 4.314 mmol) was added at 0° C. and the mixture was stirred for 10 min. The reaction mixture was allowed to warm to ambient temperature and refluxed for 3 h. The solvent was removed under reduced pressure at 45° C. and the crude reaction mixture was quenched with saturated NaHCO3 solution and extracted with DCM. The organic layer was separated and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield the title compound as a solid (1.04 g, 98%).

Provenance & Evidence