o -Toluic acid on reaction with Br_2+Fe gives

$-\mathrm{CH}_3$ group is $o$ - and $p$-directing group, however $-\mathrm{COOH}$ group is meta directing, thus the new entering electrophile occupies the position which should be $m$ - with respect to $-\mathrm{COOH}$ group and $p$ - with respect to $-\mathrm{CH}_3$ group.