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Chlorobenzene will react with hydroxide to give phenol. But will the reaction on Chlorobenzene also work with methoxide, to give anisole?

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    $\begingroup$ Note that it takes brute force or good catalysts to turn chlorobenzene into phenol. SciFinder gave me a few results (10 % of what I got for phenol) of turning chlorobenzene into anisole with heat and catalysts. None from the early 20th century though, so either they didn't boil it in methanol or it didn't work directly. $\endgroup$ – Jan Aug 28 '15 at 12:41
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Yes, It will. It's a Nucleophilic Substitution reaction,

Chlorobenzene + Sodium Methoxide --> (Under extreme conditions ) Anisole

Extreme conditions because Aryl halides don't go Nucleophilic Substitution easily.

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    $\begingroup$ Without other electron withdrawing groups on the ring I'm not so sure that it is a nucleophilic substitution reaction. The reaction could proceed through an aryne intermediate. $\endgroup$ – ron Aug 28 '15 at 15:12
  • $\begingroup$ Actually my chemistry prof told me that it will go thu Nu Substitution, I am just sharing knowledge here $\endgroup$ – Connor Verlekar Aug 29 '15 at 2:44

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