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View Full Version : Friedel crafts reaction - indole -> auxin


chazz
2008-06-20, 19:08
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.

JoePedo
2008-06-21, 01:37
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.