Chlorosuccinimide → tert-butyl 3-chloro-1H-indole-5-carboxylate

Participants

Reaction Steps

A solution of 389 mg (1.79 mmol) tert-butylindole-5-carboxylate in 12 ml methanol is mixed with 335 mg (2.50 mmol) N-chlorosuccinimide and stirred at room temperature overnight. The methanol is removed by rotation and the resulting residue is taken up in 15 ml ethyl acetate. The organic phase is washed twice with 1M sodium hydrogen carbonate solution, dried on sodium sulfate and concentrated by rotation. Column chromatographic processing of the residue on silica gel (flow agent: hexane/ethyl acetate 9:1) yields a solid.

Provenance & Evidence