Answer: D
Reduction gives 4-methylaniline, whose NHCOCH3 derivative (acetamido group, stronger director than CH3) is brominated ortho to nitrogen. After hydrolysis and deamination the Br is meta to CH3, giving 3-bromotoluene. Direct bromination of 4-nitrotoluene puts Br ortho to CH3 and ends as 2-bromotoluene, Br2 water gives dibromination, and CuBr gives 4-bromotoluene.