How do I add bromine to this molecule?

Question

If you have the molecule 1-chloro-3-iodobenzene, what steps are needed to add a bromine to the #5 position.

The #5 is meta to both the #1 and #3 not ortho or para.

Answer 1

You have two problems:

1) The halogens already on the ring, despite being o,p-directors are also deactivating, so it may be very tough to even get a third group on the ring.
2) As mentioned, they're o,p directors, so you're most likely going to get some combination of the bromine on the 4 or 6 position, with some small amount of it in the 2 position. The 5 position is the last place it wants to go.

Answer 2

Use Br2 and FeBr3. Notice that #5 is ortho to position #1 and para to position #3. The halogens are deactivators but are ortho -para directors. Iodine will somewhat enhance the reactivity of the benzene ring.