[robvba]

How would you synthesize a benzene with one equivalent deuterium?
One way i can think of would be to
1. add Br with an Fe catalyst
2. then add Mg
3. then add D2O to displace MgBr
and you should have a benzene with one equivlanet deuterium.

Is there another simple way of adding a deuterium to a benzene?

[azmanam]

that sounds pretty good to me.

you might be able to do a Bergman Cyclization (http://name.howtochem.com/bergman-cyclization/) where you've exchanged one of the terminal alkyne protons for deuterium (take starting endiyne, deprotonate x1eq base, quench D2O). 

but there's nothing wrong with your route. (except you need Br2 and FeBr3 as reagents step1)

[robvba]

so using the Bergman cyclization i can
1. treat enediyne with heat or light
2. use tertBuO- to strip an H+
3. add D2O to add one equivalent D

does that sound right?

[azmanam]

other way around.  1 eq base on the enedyne to deprotonate.  1 eq D2O to add one equiv D.  then heat/light + cyclohexadiene.

[robvba]

thank you.

what about:

1. add Cl2 + FeCl3 to benzene
2. add 2Li in hexane
3. add D2O

[lutesium]

Just out of curiosity why do you need that compound???


Lutesium...

[robvba]

this is for an organic chemisty class and my own understanding. It will not be synthesized in a lab.