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The required transformations are:
- Bromination at position 2
- Conversion of $$-NO_2$$ to $$-Cl$$
- Oxidation of $$-CH_3$$ to $$-COOH$$
Bromination must be carried out first. In 4-nitrotoluene, the $$-CH_3$$ group is ortho/para-directing and the $$-NO_2$$ group is meta-directing; both direct bromination to position 2.
$$\text{4-Nitrotoluene} \xrightarrow{Br_2/Fe} \text{2-Bromo-4-nitrotoluene}$$
The nitro group is then reduced to an amino group.
$$-NO_2 \xrightarrow{Fe/H^+} -NH_2$$
The amino group is converted into a diazonium salt and subsequently replaced by chlorine via the Sandmeyer reaction.
$$-NH_2 \xrightarrow{HONO} -N_2^+Cl^- \xrightarrow{CuCl} -Cl$$
Finally, the methyl group is oxidized to a carboxylic acid.
$$-CH_3 \xrightarrow{KMnO_4} -COOH$$
Thus, the correct sequence is
$$Br_2/Fe \;\rightarrow\; Fe/H^+ \;\rightarrow\; HONO \;\rightarrow\; CuCl \;\rightarrow\; KMnO_4$$
Hence, the correct answer is
$$\boxed{\text{Option D}}$$
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