Author Topic: Benzotrifluoride acylation?  (Read 1779 times)

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Nemo_Tenetur

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Benzotrifluoride acylation?
« on: May 12, 2002, 11:00:00 AM »
I require some trifluoromethylpropiophenone and trifluoromethylvalerophenone as precursors for controlled substance analogs. Unfortunately, my textbook told me that direct acylation of benzotrifluoride wouldn't be possible. If you heat a mixture of benzotrifluoride and propionylchloride with aluminum chloride, the result is benzotrichloride and hydrogen fluoride.
Anybody know a useful catalyst for direct acylation ?

psychokitty

  • Guest
Triflouromethyl group deactivating
« Reply #1 on: May 14, 2002, 11:36:00 AM »
I don't think direct acylation will work due to what I would guess is the deactivating nature or the triflouromethyl group. 

You could form the benzaldehyde first (maybe) and then go with a grignard reaction to get the alcohol which could then be oxidized to the ketone.  Just an idea.

I'll hit the library sometime soon and see what I can find.