[buRnINGbeND]

sure you're going to get some rearrangement

I was taught is was mostly rearrangement rather than some rearrangement, but I may be mistaken.

but if you really want to do it that way, you should be iodinating, not brominating, and you only need one reduction step.

Why iodination? There is a large amount of literature addressing Sonogashira coupling with aryl bromides (and chlorides), which are easier to make than iodides.

What did you have in mind for the one step reduction?

iodine rate>bromine rate>chlorine rate and yields as well.

and for one step reduction all you have to do is catalytic hydrogenation.  just don't use Rh or Ru or too excessive pressures/temperatures that you reduce the aromatic ring basically.

[Dan]

and for one step reduction all you have to do is catalytic hydrogenation.

Sorry, I was being slow and forgot the alcohol after ketone hydrogenation is benzylic and will undergo hydrogenolysis.