[asd34]

Just for paper work I have to solve this. I wrote one possible solution but in few steps I'm not sure. For ex. with the Bechamp reduction, it is possible to reduce the carboxyl group too? Or in the second step, can I get a dibromo, or it is up to the bromine equivalency? And finally, there is a shorter way to get the product?

[Schrödinger]

I can think of a shorter way. But I certainly have no idea about the yields or the practical difficulties involved.
1. Oxidize toluene to benzoic acid
2. Nitrate it and reduce the nitro compound to 3-aminobenzoic acid.
3. Brominate. Due to ortho effect, the Br that comes in will be ortho to the COOH group. I dont think polybromination will be a problem, considering that the system is kinda deactivated thanks to the COOH group present. Steric factors may also prevent tribromination.
4. Now convert the amine to N₂ and form the cyanide from here.

[asd34]

I can think of a shorter way. But I certainly have no idea about the yields or the practical difficulties involved.
1. Oxidize toluene to benzoic acid
2. Nitrate it and reduce the nitro compound to 3-aminobenzoic acid.
3. Brominate. Due to ortho effect, the Br that comes in will be ortho to the COOH group. I dont think polybromination will be a problem, considering that the system is kinda deactivated thanks to the COOH group present. Steric factors may also prevent tribromination.
4. Now convert the amine to N₂ and form the cyanide from here.

Thank You!

[Schrödinger]

Yeah, it all sounds theoretically fine. But the experimental aspects havent been taken into account. The method I outlined is in all probability a very bad synthetic route So, I'd like it if someone with experimental background can verify this.