[Doc Oc]

I'm having a strange problem.  I have a linear amide with a primary alkyl bromide.  I am attempting to phenoxylate the compound, but instead I am seeing substitution at the amide and preservation of the bromine!  I've used several different solvent/base combos (DMF, DCM, acetone, Et₃N, K₂CO₃, pyridine, proton sponge) with cooling/heating/neither, none of them giving a different result.  I can't say I've ever seen this happen and I'm rather surprised.  Does anybody have any suggestions on how to solve this?  I'm about at my wit's end.

[Dan]

That's pretty fruity. What's the amide, something active like an acyl pyrrole?

Not the cheapest solution, but maybe try silver phenoxide - the Ag⁺ should strongly activate the alkyl bromide.

You could also bulk up the amide.

[Doc Oc]

Morpholine!  I like your suggestion and I should have thought of it since I've used silver salts in challenging alkylations in the recent past.  Thanks for the refresher Dan.