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Topic: multi step synthesis help  (Read 3041 times)

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Offline cincanales

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multi step synthesis help
« on: April 17, 2011, 08:17:32 PM »
Can anyone help me with this multistep synthesis

Surplus reactant is ethyne
The intermediate product is 1-[4-(but-2-ly)-3-nitrophenyl]ethanone

The ultimate product is 3-[4-(1-ethoxybutyl)-3-fluorophenyl]butan-1-ol

So far I have started with toluene br2, heat
-c triple bond ch

1. NaNh2 2. Ch3Cl

1. Ch3C=OCl AlCl3 2. H2O

HNO3, H2SO4

SN,HCl

H2NNH2, -OH

NaNO2, HCl

HBF4, heat

NBS, H2O

NBS, H2O

Then this where I get confused and lost I don't know how to attach Ch2Ch2OH to ethane.
How would I go about adding OCh2Ch3 to ch2c-br=chch3? I'm confused can anyone please help me I would greatly appreciate it. Is there another way to get the ultimate product?

Offline Honclbrif

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Re: multi step synthesis help
« Reply #1 on: April 17, 2011, 09:55:09 PM »
Could you provide some structures? Its a little hard to follow in text alone.
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