Why is the Friedel-Crafts alkylation of nitrobenzene disfavoured?

Suggest a synthetic route to m-nitrotoluene, starting from benzene.

The conversion can be achieved in two ways:

$\hspace{10 mm}$

or:

However, the first route is not possible as the Friedel-Crafts reaction does not yield a meta-substituted product. Why is that so?

• Hmm, I don't like second reaction either, you have proof it would work? – Mithoron Dec 22 '15 at 22:28
• Also, I don't believe Na will leave that nitro group intact. – Ivan Neretin Dec 23 '15 at 6:35
• The use of a methyl halide does not seem feasible to me, as it suggests that the electrophile would be a methyl carbocation, which does not form in practicality. I would imagine otherwise that – Sterling Cavanaugh Apr 30 at 2:39