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Topic: Transform alkyl halide to aldehyde  (Read 8409 times)

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Offline rolypoly

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Transform alkyl halide to aldehyde
« on: November 12, 2007, 12:29:26 PM »
Hi there.

I am working in a polymer organic lab and need help in a step in a synthesis.  I have an alkyl chain (dibromo butane) in which I have protected one side of it with phthalimide group.  The other end of the chain needs to be transformed to an aldehyde.  The halide can also be transformed to an alkene which I can hydrolyze into an primary alcohol and finished with the Swern Oxidation into an aldehyde.

So if anyone has a robust and clean reaction to change the alkyl bromide into an aldehyde...*delete me*

P.S-I can't use the Grignard reaction b/c I need a four carbon chain backbone.

Roly Poly

Online sjb

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Re: Transform alkyl halide to aldehyde
« Reply #1 on: November 14, 2007, 06:10:04 AM »
How about RCl -> an alkyl phosphate or similar, hydrolyse and then oxidise as an alternative.

It's a shame you already have the 4-carbon chain in place.

Can you try phthalimide + *1,3-dihalopropane*, then oxidative insertion of CO, and depending on what you get out of that, reduction of the acid / acyl halide / ester ... down to the aldehyde. There are safer alternatives to using neat CO, if that's a concern...?

S

Offline Shaun

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Re: Transform alkyl halide to aldehyde
« Reply #2 on: November 21, 2007, 10:15:37 AM »
There are a number of ways to do this according to Larock.  This is a great reference - wherever there's an organic chemist you can be sure a copy of this is nearby.

Ag+, base, DMSO

4-(dimethylamino)pyridine N-oxide, DBU

etc. etc.

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