Chlorobenzene is synthesized by the electrophilic substitution of benzene with chlorine in the presence of a Lewis acid catalyst such as anhydrous $\text{FeCl}_3$ .

$\text{C}_6\text{H}_6 + \text{Cl}_2 \xrightarrow{\text{Anhyd. FeCl}_3} \text{C}_6\text{H}_5\text{Cl} + \text{HCl}$

Option 3 is incorrect because the Sandmeyer's reaction, which is also used to prepare chlorobenzene, requires aniline (not phenol) to react with $\text{NaNO}_2$ and $\text{HCl}$ to form a benzene diazonium halide, which is subsequently treated with cuprous chloride ($\text{CuCl}$) .