Qustion about leaving groups and bases

[invain]

If I had a nucleophile, say the conjugate base of benzene, and a molecule with a bromide, and a primary alcohol. Would the nucleophile attack the carbon bound to the bromide, or the proton on the alcohol?

If it's hard to follow I can try to make a picture. Basically I want to add Isobutanol to benzene using a bromide leaving group. (2-bromo-2-methyl-propanol). Possible? I don't know if the alcohol would act like an acid or would the bromide leave first.

 

[Nemus]

This doesn't work. First, as you suspect, the phenyl anion will pick up the proton from the alcohol and return to benzene. Two, if you protect the alcohol as e.g. a benzyl ether, it will still be too crowded around the bromine for this to work.
Maybe you could fish some of the correct structure out of you use AlCl3 catalysis instead but this reaction (Friedel-Crafts alkylation) is notorius for giving messy mixtures. And the alcohol group certainly doesn't help.
Why do you need this awkward compound? Can't you make something sensible?