[Woodwardt84]

Hi guys

I have been doing NAS on 4-Bromo-2-fluorobenzonitrile. Is it possible to do NAS on 4-bromo-2-fluorobenzamide? I don't see why it shouldn't but some people in my surroundings claim that it is more difficult on an amide than a nitrile. Any experiences?

[Arctic-Nation]

The reaction will work, but more slowly than with the nitrile because amide is a weaker electron-withdrawing group.

A different problem that might pop up is that if your nucleophile is a strongish base and your amide is primary or secondary, the amide or its anion might take over the role of the nucleophile. Don't have any practical experience with this, though.

[Woodwardt84]

The reaction will work, but more slowly than with the nitrile because amide is a weaker electron-withdrawing group.

A different problem that might pop up is that if your nucleophile is a strongish base and your amide is primary or secondary, the amide or its anion might take over the role of the nucleophile. Don't have any practical experience with this, though.

I have substituted the flour in the benzonitrile with Butanol and heptanol, deprotonating the alcohol with Cesiumcarbonate. I don't think the protons on the amide should be a problem.