[AndEEDJay]

hello chemistry lovers from all over the world
I'm new on this forum, but I already have a question
please tell me how to synthesis the 2,3,5-tri-iodo-benzoic acid starting from benzene
thank you very much and I hope is interesting for you too xD
by the way...there is a picture bellow if I didn't spell well..

[Dan]

You must show that you have attempted the question. Please read the Forum Rules.

[AndEEDJay]

ok, I wrote here my ideas
I guess this is the way

nitration of benzene->nitro-benzene

then reduction of the -NO2 group which turns into NH2

now you have more possibilities because you can put NaNO2+HCl->HNO2+H2O and make that diasonium salt and then with KI you can put the I on the benzene ring

you may want to block the p position the ring with SO3H and when you don't need it anymore you can put some water vapours to eliminate it because that position must be empty finally

and the acylation method to protect the amino group from HNO3 which we all know that has an oxidizing character too; after the nitration you can hydrolasis and get the NH2 group back

I guess this is the way but I can't really obtain it because of those hard positions to reach: 2,3,5
I thought too of a steric obstruction but I let you choose the right method
thanks and sorry for bad spelling..

[curiouscat]

Writing with a mouse can be fun! 

[AndEEDJay]

sorry for that but I don't know other method to show you my ideas
I read that scanned attachments aren't allowed or something like this
I know more chemistry than English and I thought is better to draw than simple writting
if you have any ideas please post anyway, because more ideas are better than only one
and together we can make it for sure
it's a challenge from one of my chemistry teachers and I can't solve it (I think of it for more than two months and I don't get the right point)

[AndEEDJay]

anyone any other ideas?

[tomek]

Make anthranilic acid first. Then iodinate it with ICl. Next goes diazotization and KI treatment.

[AndEEDJay]

thank you very much
it is a good idea