Appropriate Substitution Reactions
  1. Bromine may be introduced by heating with Br2 and a Fe+3 catalyst.
  2. Nitro groups may be introduced by heating with conc. HNO3 and H2SO4.
  3. A carboxyl group may be created by KMnO4 oxidation of the methyl group.

Which reaction would you choose for the first step?

  heating with Br2 and a Fe+3 catalyst
  heating with conc. HNO3 and H2SO4
  heating with aqueous KMnO4