Radicals only do a few things. Halogen abstraction, proton abstraction, reproportionation, adding to alkenes and alkynes.
In your molecule, you pretty much have two kinds of protons. Is it going to do proton abstraction from the 2° carbon or the 3° carbon is the basis of this question.
I am unsure about how selective the hydroxidy radical is, but the bromine radical would exlcusively abstract the 3° proton. Chlorine is around only 60% for that proton. The fact that you have 2 protons on a 2° carbon makes it statistically more likely, but the 3° carbon-H bond is weaker making it easier to abstract.