[electerr]

Hi!

I'm doing a synthesis of 2,4,6-tribromoaniline using aniline and Br2 (excess) with acetic acid as a catalyst. I know that the reaction only gives a maximum 50% yield and I know that it must be that there are side reactions but I can't figure out what these reactions are! I know that the amine-group can be protonated in an acidic enviornment thereby becoming a meta-directing, deactivator and giving a meta-substituted by-product but.. it seems as though acetic acid would be too weak of an acid to protonate enough molecules of aniline to give a high yield (50%) of meta-substituted by-products...

I know that there is a possibility also that all the substitutions do not take place and a di- or tri-substituted product can be formed. This seems as though it would also be a small procent of the reactions which take place.

Can anyone help me figure out the other side reactions or is the meta-substituted product and di- or tri-substituted products the only ones!?!
Thanks in advanced!