Question

I have to write a synthesis (just below) of a molecule and propose reactants and conditions :

But I have a problem with the 2nd step. Where I need to do the ether.

Apparently it's very difficult to deprotonate the H of the allylic alcohol, so I can't use NaH on it and then react it with the nitrobromobenzene.

Instead, I have to activate the electrophily of the C next to the Br and I really don't know how can I do.

My proposition is that I can reduce the bromobenzene by using the NADH and reductase so I can have an NH2 and then by delocalization I can have a very electrophilic position where the alcohol can react and I will use a base like NEt3 to deprotonate. I am not very sure about that.

Answer 1

To perform the ether formation in the molecule synthesis, an alternative approach is needed. One possibility is to reduce the bromobenzene to have an NH2 group, which can react with the alcohol. A base like NEt3 can be used to deprotonate the alcohol.

Step-by-step explanation:

The reaction described involves the synthesis of a molecule and the challenge of performing the ether formation. The allylic alcohol cannot be deprotonated easily using NaH, so an alternative approach is necessary.

One possibility is to activate the electrophilicity of the carbon next to the bromine and then react with the alcohol. This can be achieved by reducing the bromobenzene to have an NH2 group, which can then react with the alcohol. A base like NEt3 can be used to deprotonate the alcohol.