[darkdevil]

Hi,
I wonder if I can do a blanc chloromethylation on this compound and add a chloromethyl group to its aromatic carbons?

[Archer]

Unlikely, two deactivating groups will not favour electrophillic substitution.

Which position do you want the group? You may be able to achieve it via an alternative route.

[darkdevil]

Unlikely, two deactivating groups will not favour electrophillic substitution.

Which position do you want the group? You may be able to achieve it via an alternative route.

Hi, I want the group to be on any position on the aromatic ring. Even halogenation on the aromatic  is fine. How about using NBS to brominate the aromatic ring?

[Archer]

Does this have to be your starting material?

The issue, as I see it, is that the NO₂ tends to deactivate the ring quite strongly. Indeed, Friedel Crafts Acylations are sometimes conducted using nitrobenzene as the solvent.

Carbonyl's also deactivate the ring quite strongly too, that is why the Friedel Crafts does not often acylate the aromatic ring twice.

 How about using NBS to brominate the aromatic ring?

That I don't know, I would have to open this up to one of my colleagues who may have experience of this. If I wanted this molecule, for example:



I would chose another starting material and go via another route.