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