Synthesis of 4-Iodo-3-nitrobenzamide

[ChemistTree]

I have to synthesize 4-Iodo-3-nitrobenzamide using a starting product that contains no more than 8 carbons. The materials have to be purchased so they must be reasonable in price as well. I was thinking about starting with Iodobenzene since it is an Ortho/Para director. After that I was thinking about adding the amide group but I am unsure of how I want to do the addition. A nitro addition would come after and that should add in the correct place because both substituents would direct it appropriately. Any suggestions on how to prepare the amide and then actually react it with the iodobenzene? Thanks in advance

[Caffeinated Chemist]

https://docs.google.com/viewer?url=www.google.com/patents/US5464871.pdf

 

If you look at page 13 they outline how to synthesize 4-iodo-3-nitrobenzamide from a starting material of 4-iodo-3-nitrobenzoic acid. I looked up prices and it's pretty expensive. Maybe you could synthesize your own 4-iodo-3-nitrobenzoic acid? I wish I could help more. Good luck!