How to Synthesize C6H5D from Benzene: A Creative Approach

[kchemistry]

Homework Statement

Hey guys,

Our prof gave us a random question for our lab report: how do you get C6H5D from benzene? We've never gone over this rxn, and I can't find it in the text or online. I can't think of a way for benzene to substitute like that.

Thanks, I appreciate the help.

Homework Equations

The Attempt at a Solution

 

[epenguin]

Although you probably won't easily find this reaction online etc. - I guess it's not a thing anyone often needs to do - it's an exercise for some controlled creativity using reactions that you have done or can find online. Not a unique answer I would say, but some might be better than others.