[DavidF]

hey folks

i was wondering why the following transformation won't work with the appropriate amide (acyl attached to the NH2) to yield the final product from the starting reagent ?



thanks !

[macman104]

I'm not sure how efficient the displacement of the bromine by the ammonia will be.  Have you learned the sandmeyer reaction, with the diazonium salt N₂⁺?

[DavidF]

yes, but the original question refers to whether i can get the final product with a Friedel Crafts reaction instead

[kimyaa2]

ummm all i know is that friedel craft will give no reaction when the benzene ring has a strongly deactivating group..

[UnintentionalChaos]

hey folks

i was wondering why the following transformation won't work with the appropriate amide (acyl attached to the NH2) to yield the final product from the starting reagent ?



thanks !

I seem to be missing what you are talking about. Do you mean the half-amide, half-chloride of carbonic acid? That material cannot be prepared and would readily polymerize into a polyimide with loss of HCl. If you were to protect the amine somehow, you'd still be left with the problem of reducing the carbonyl functionality.

You can replace the first two steps with this reaction: http://en.wikipedia.org/wiki/Blanc_chloromethylation

You'll need to use a vast excess of ammonia for the last step due to the fact that alkylated amines are better nucleophiles and therefore preferentially alkylated multiple times if given the opportunity.