# Do Grignard reagents deprotonate amines?

Can I add Mg/dry ether to 2,4,6-tribromoaniline followed by $\ce{D2O}$ in order to replace the bromines with deuterium?

The reaction I'm proposing is part of a synthetic route as shown below.

• Amine or amide? Apr 12 '16 at 16:34
• Amine. The picture shows the conversion to be done, and I'm with TriBromo anilene trying to replace it's Br s with D Apr 12 '16 at 16:41
• Yes, it will deprotonate tribromoaniline Apr 12 '16 at 17:02
• you can never use Grignards in presence of acidic protons. Apr 13 '16 at 6:37
• @gannex Usually true, but if you have an excess of Grignard and the deprotonated species still reacts with the surplus Grignard, you might be able to get away with it. It is a wasteful way to use Grignard reagents, though. And in this case it risks throwing away a lot of the substrate. Apr 13 '16 at 15:48