Quantitative benzylic mono- and gem-dibromination on primary aromatic amine derivatives have been achieved using molecular bromine and by protecting the amino group as a succinimide moiety. The reactions of N-(o/m/p-tolyl)succinimides 5a-c with 1.25 equivalents of molecular bromine in CCl4 at room temperature furnished the corresponding benzylic monobrominated products 6a-c in 92-94% yields, while with 2.5 equivalents of molecular bromine in refluxing CCl4gem-dibromo products 7a-c were obtained in 94-96% yields. It is also possible to carry out nuclear bromination in these N-protected primary aromatic amines at an alternate site by using suitably substituted aniline derivatives. Thus the reaction of 3 with 1.25 equivalents of molecular bromine in acetic acid gave the desired monobrominated product 4 in nearly 100% yield. NCL Communication No. 6615.