[cara]

I am looking for a way to convert an aromatic nitro compound to the aromatic fluoride.  My substrate contains an hydroxy substituent ortho to the nitro group.  The standard balz-shiemann reaction will not suffice due to the polar substituent.  Alternative methods to the BS reaction that I have found, uses HF - which I am trying to avoid

[cundi]

I think it is not easy transformation.
You could try to protect the hydroxygroup as ester in order to decrease the electrodonor capacity of this group. (Maybe a CF3CO-OAr-NO2). Just an idea. I don't know if it will work.

Good luck.

[orgopete]

I suggest you look in Modern Fluoroorganic Chemistry, Peer Kirsch. From my notes, there are a number of synthetic procedures that you might find interesting. Perhaps the electrophilic fluorine reagents would be a good alternate. I see there is a reference for phenol to ortho-fluorophenol with an electrophilic fluorine reagent.

If you cannot get the book in your library or interlibrary loan quickly enough, you might try Google books, that was how I learned of this book.

[lavoisier]

I am looking for a way to convert an aromatic nitro compound to the aromatic fluoride.  My substrate contains an hydroxy substituent ortho to the nitro group.  The standard balz-shiemann reaction will not suffice due to the polar substituent.  Alternative methods to the BS reaction that I have found, uses HF - which I am trying to avoid

Why do you say the neighboring OH group would stop the BS reaction from working?
Is it not:
ArNH₂ --> ArN₂⁺BF₄^- --> ArF + BF₃ + N₂
I would still try it on a small scale, you never know.

If you have tried it and it hasn't worked, you can also try non-aqueous systems, e.g. doing the diazotisation with tBuONO in the presence of BF₃.Et₂O, you should get the fluoride directly. Maybe the boron will even bind to the oxygen and stop it from interfering with your reaction, who knows?

Otherwise, I agree with cundi, you can protect this OH, but I would avoid esters because you might get a cyclisation.