Aromatic Organic Synthesis help

Feb 2014
2
0
The question reads:
Treatment of A in dibromomethane with one equivalent of aluminum tribromide yielded B as the only product in 78%. Draw a curved arrow mechanism for this transformation.


I've got this first part figured out, I'm just completely lost on the second part. I really have no idea why this would happen.

The second part reads:
However, when three equivalents of aluminum tribromide were used with A, compounds C and D were obtained in a combined yield of 97% after neutralization of the reaction mixture with sodium bicarbonate solution, followed by standard workup. Suggest an explanation for these observations and draw a curved arrow mechanism showing how the ether group in C was converted to Phenol.


I'd really appreciate anything here, I'm kind of lost on the second part.