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

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ADDENDUM: This is otherwise known as:

2-[1-(4-bromophenyl)-1-phenylethoxy]-N,N-dimethylethanamine
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Answer 1 · 2016-08-17T23:52:04

Here's what I get for a retrosynthesis.

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

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

Step 1

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.

Step 2

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

Step 3