[Dibromofunkatol]

Hello,

I have a starting compound of what appears to be a primary Arylamine, Ar-NH2.
From that I want to make a phenyl ethyl ether, Ar-O-CH2-CH3.

This is what I have attempted:
Start With AR-NH2
React 1: Diazotination: HONO, HCL, 0 degrees Celcuis
Product 1: AR-NN+ (Diazonium ion)
React 2: Sandmeyer Reaction: Cu2O, Cu 2+, H20
Product 2: AR-OH
React 3: NaOH
Product 3: AR-O- ?
React 4: Primary Alkyl Halide Reaction? : CH3CH2I
Product 4: AR-O-CH2-CH3

Would this work?

Thanks

[Rabn]

There must be a mechanism through which you could substitute ethanol directly releasing NH₃.

[Dibromofunkatol]

Are you referring to the NN⁺ ion?  There isn't a NH₃ group in the problem.  It's NH₂ and to my understanding that directs any attack on the aryl ring to the ortho and para positions. 

[macman104]

There must be a mechanism through which you could substitute ethanol directly releasing NH₃.

None that I'm aware of.  I forget the exact reagents that for the Phenol formation, but the williamson synthesis you've proposed seems fine.

EDIT:  Dibromo, I believe Rabn, is talking about substituting directly the ethanol, in which, you would have to do something with the H on the ethanol, so then you'd lose NH₃, but I don't know of any way to do that.

[Dibromofunkatol]

Ok cool, I'm going to go with it.  Thank you both.

[agrobert]

Why not work up you diazo salt NN+ with ethanol instead of water.  Definitely plausible but may be tricky to do it anhydrously.