Synthesizing 2-bromoaniline from bromobenzene I am trying to synthesize 2-bromoaniline from bromobenzene. I came up with a reaction path, but I want your thoughts on whether this is feasible and can produce a decent yield.

Sulfonation of bromobenzene (to block the para position)
Nitration of the product from (1). This should produce 4-bromo-3-nitrobenzenesolfanic acid.
Reduction of the nitro group via Zn(Hg) and HCl (to turn the NO2 group into NH2).
Reverse sulfonation (to get rid of the sulfonic acid group).

And the final product from this should give 2-bromoaniline. Should this theoretically produce a decent yield even if bromobenzene is slightly deactivated?
It will be much quicker to run the direct nitration of bromobenzene and isolate the ortho nitro product by chromatography. It is the minor nitration product, but your overall yield will be better by cutting out two steps which will give only moderate yields.
Nitration and chromatography procedure here 1