How chlorobenzene is obtained from aniline?
How about diazotization followed by a Sandmeyer reaction?
Diazotization is the reaction of an unsubstituted aromatic amine with nitrous acid to form an aromatic diazonium salt.
Usually, sodium nitrate and hydrochloric acid react at 0 °C to 5 °C to generate the nitrous acid in situ.
The Sandmeyer reaction
The Sandmeyer reaction is the