ABSTRACT. A large scale and commercially feasible synthesis of 5-chloroindole and its 3- substituted analogues has been described via a halogen-halogen exchange reaction from 5- bromoindole and its derivatives using cuprous chloride and dipolar aprotic solvent N-methyl- 2-pyrrolidone in one pot with good yields. Keywords: 5-haloindoles, copper (I) chloride, N- methyl-2-pyrrolidone, halogen-halogen exchange.