4-Nitrotoluene is brominated with $\mathrm{Br}{}_2$ and $\mathrm{FeBr}{}_3$ (ring bromination). The major product is

The methyl group directs ortho/para and the nitro group directs meta. The positions ortho to $-\mathrm{CH}{}_3$ are also meta to $-\mathrm{NO}{}_2$, so both groups reinforce each other there. Bromine enters ortho to the methyl group, giving 2-bromo-1-methyl-4-nitrobenzene. The position ortho to $-\mathrm{NO}{}_2$ is deactivated and not favoured.