Question

How do you do a retrosynthesis of {2-[1-(4-bromophenyl)-1-phenylethoxy]ethyl}dimethylamine?

ADDENDUM: This is otherwise known as:

2-[1-(4-bromophenyl)-1-phenylethoxy]-N,N-dimethylethanamine
http://www.molbase.com/en/3565-72-8-moldata-1025875.html

Answer 1

Here's what I get for a retrosynthesis.

Explanation:

You don’t identify the starting materials but, if I haven’t gone back far enough, you can probably develop appropriate retrosyntheses.

I'm starting with benzene, acetic acid, ethylene oxide. and dimethylamine.

The structure of 2-[1-(4-bromophenyl)-1-phenylethoxy]-N,N-dimethylethanamine is

(From www.chemspider.com)

The central part of the molecule is an ether. We could do a retro-Williamson ether synthesis.

Retrosynthesis of the (N,N-dimethylamino)ethyl chloride is relatively straightforward.

We can make the chloride from an alcohol, and the alcohol comes from the reaction of dimethylamine with ethylene oxide.

The remaining retrosyntheses are mostly combinations of Friedel-Crafts and Grignard reactions.