Step 1:
(∵NO2 is m-directing group while CH3 group is o− and p− directing group. Thus, Br group attach at o− position with respect to CH3 and m-position with respect to NO2 group)
Step 2:
On reduction with Sn/HCl,NO2− group changes to −NH2 group.
Step 3:
On treatment with NaNO2+HCl;NH2 changes to diazo group.
Step 4:
On treatment with H3PO2, only diazo group (N2Cl) reacts and gets removed.
Step 5:
On oxidation with KMnO4/OH−,−CH3 group changes to −COOH group.





