[AndersHoveland]

I am wondering if there is an easier route to preparing 2-Iodotoluene.
Limited nitration of toluene results in 2-nitrotoluene (90% isomer selectivity).
Would refluxing the 2-nitrotoluene with KOH result in 2-hydroxy-toluene (alternatively 2-methyl phenol) ?

This could then be distilled with potassium iodide and concentrated phosphoric acid to give the desired 2-Iodotoluene.

Or if reacting iodine with toluene in sunlight, is there a good method to distill out 2-Iodotoluene, isolated from other isomers? The yields for this would probably be very low.

The 2-Iodotoluene can then be oxidized with KMnO4 to 2-Iodobenzoic acid, and then oxidized further to the useful regent 2-Iodoxybenzoic acid, using chlorate with sulfuric acid. 2-Iodoxybenzoic acid is useful for selective oxidation of alcohols to aldehydes. Although the synthesis of this regent is typically fairly complicated, the regent can be reoxidized/recycled after each use.