Aromatic Substitution in acidic medium
Three parts to this answer:

You have two electro-philes, the tertiary carbo-cation formed by protonating the alcohol and breaking off a water molecule and then the bromine.  Looks like you got this part.

Assume the two electro-philes attack consecutively.  The methoxy group is more strongly activating and ortho/para directing than the alk-yl group for the second attack.  So the bromine and the newly formed carbon-carbon bond will be meta to each other.

The sterically favored positions for each are as shown in the given answer.  The carbo-cation favors the position para to the methoxy group.  The bromine picks the position ortho to the methoxy group that's away from the alk-yl function.


Please excuse my use of hyphens.  Device auto-correct was putting in wrong words and I had to defeat it.