Ether cleavage with conc HBr
Cleavage of ethers using strong acids (classically $\ce{HI}$ but $\ce{HBr}$ should work as well) can proceed by either an $S_N1$ or $S_N2$ mechanism. In this case the cation formed would be primary or phenyl, neither of which are stable, and so the reaction proceeds via an $S_N2$ mechanism.



The oxygen is protonated in an equilibrium reaction. The bromide ion then attacks at the least hindered carbon and the $\ce{C-O}$ bond breaks in a concerted $S_N2$ mechanism.

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