Chlorosuccinimide → Methyl 2-chloro-1H-indole-3-carboxylate

Participants

Reaction Steps

A stirred suspension of methyl indole-3-carboxylate (6.0 g, 0.034 mole) in chloroform (200 ml) was treated with N-chlorosuccinimide (5.04 g, 0.038 mole) to afford a clear solution within 15 minutes. After 2 h at room temperature this was treated with 1M HCl/ether (34 ml, 0.034 mole) and allowed to stir for a further 1 h, then treated with excess 10% Na2 CO3 solution and the chloroform layer separated, dried (Na2 SO4) and concentrated in vacuo. The residual yellow solid was recrystallised from chloroform/60-80 petrol to afford the title compound (D 11a) as a beige solid (3.4 g, 48%).

Provenance & Evidence