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The best method (as I have read) for preparation of chlorobenzene is by reacting it with $\ce{Cl2}$/$\ce{FeCl3}$. Why its not the best practice to react phenol with $\ce{PCl5}$ ?

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Well you see, phenol do not react with PCl5 to give chlorobenzene as it undergoes EAS mechanism.In order to make the reaction possible you will have to activate phenol with nitro group.

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  • $\begingroup$ well how can you activate phenol by nitro group ? nitro group is deactivating in nature. $\endgroup$ – Abhirikshma Feb 8 '16 at 6:03
  • $\begingroup$ I mean to say activate it towards nucleophilic attack $\endgroup$ – Ja Crispy Feb 8 '16 at 7:10

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