[HP]

Indeed not completely

[victor]

Nitro group easy for remove too. First hydrogenation it with nascent H for example with Zn/HCl. The formed amine then diazotation with NaNO2/HCl and the formed diazonium chloride salt may be eliminated with H3PO3...

But nitro group deactivate aromating ring towards an electrophilic substution (though in the case of anisole not completely)

Hey boss, talking about deactivator, I think that Br group also deactivates aromatic ring because of it's high electronegativity... (this discussion is getting interesting, I never imagine that it would be that interesting... )

[barcrphd]

though bromine is electronegative, it is only weakly deactivating compared to nitro group. that may be the reason why bromine is preferred over nitrogroup.

one more reason, though less significant, could be that, the use of mineral acid could cleave the ether linkage. ofcourse, with HCl the rate of hydrolysis will be very less.

[victor]

Yup, because Cl is far more electronegative than Br...