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Laboratory Tips Safety proceedures, test reagents, drilling rubber stoppers, bending glass tubes, etc. Contributed to by chemists.

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 #1 
Old 2008-06-20, 19:08
chazz chazz is offline
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Default Friedel crafts reaction - indole -> auxin

Quick question: if I did a Friedel Crafts reaction with indole and chloroacetic acid would I get indole 3 acetic acid, aka auxin? would it acetylate (is that the correct terminology?) the 3 position?

If not, how can you be selective about it? When doing this reaction with benzene to get phenylacetic acid it obviously doesn't matter which position is effected as there is only one so whats the case with indole?

Any one have any ideas? thanks.
 #2 
Old 2008-06-21, 01:37
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Default Re: Friedel crafts reaction - indole -> auxin

Quick question: if I did a Friedel Crafts reaction with indole and chloroacetic acid would I get indole 3 acetic acid, aka auxin? would it acetylate (is that the correct terminology?) the 3 position?

I believe Shulgin suggests something similar for the acyl halide of a dicarboxolic acid. Might be worth a read.
 
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