If you are not given the conditions, you should assume "ordinary" conditions.
I would consider ordinary conditions to be temperatures less than 100 °C and only "ordinary" catalysts.
Thus, the bromination of benzene at 65 °C to 70 °C gives bromobenzene as the major product.
The problem is that
You can, however, get a 93 % yield of hexabromobenzene if you heat a solution of benzene in a solvent such as tetrachloroethane (b.p. 146 °C) with 7 molar equivalents of bromine and an
The methyl group is activating, so the reaction conditions don’t have to be so vigorous to get 2,4,6-tribromotoluene.
Heating excess bromine with a solution of toluene in acetic acid and a