Chemical Reaction Sequence
1. Bromination:
CH3-NO2
Br2/Fe
⟶
CH3-NO2-Br
2. Reduction:
CH3-NO2-Br
Fe/H+
⟶
CH3-NH2-Br
3. Diazotization:
CH3-NH2-Br
HONO
⟶
CH3-N+2-Br
4. Sandmeyer Reaction:
CH3-N+2-Br
CuCl
⟶
CH3-Cl-Br
5. Oxidation:
CH3-Cl-Br
KMnO4
⟶
COOH-Cl-Br