Propose a mechanism for substitution of an aryl bromide, Chemistry

Nucleophilic aromatic substitution is possible, but involves substitution of a typical leaving group rather than a hydrogen atom. Remembering that S_N2 and S_N1 mechanisms are not viable at sp² carbons, propose a mechanism for substitution of an aryl bromide by methoxide. Rank the relative reactivates of the following substrates, justifying your answers with resonance structures of key intermediates.

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