Indole → 3-Chloro-1H-indole

Participants

Reaction Steps

To a solution of indole (2.0 g, 17.0 mmol) in DMF (12 mL) at 10° C. under a nitrogen atmosphere was added N-chlorosuccinimide (2.49 g, 18.7 mmol). The reaction was stirred for 4 h then quenched with 10% sodium bisulfite solution. After stirring for 15 min the precipitated solid was collected by vacuum filtration. The filtered solid was washed with water then dissolved in dichloromethane. The solution was washed with water, brine and dried over sodium sulfate then concentrated in vacuo to give 3-chloroindole (1.8 g, 70%) as a yellow-brown solid: 1H NMR (CDCl3, 300 MHz) δ 8.06 (s, 1H), 7.64 (d, J=7.8 Hz, 1H), 7.34-7.37 (m, 1H), 7.16-7.22 (m, 2H).

Provenance & Evidence