The Vespiary

The Hive => Novel Discourse => Topic started by: Nemo_Tenetur on May 12, 2002, 11:00:00 AM

Title: Benzotrifluoride acylation?
Post by: Nemo_Tenetur 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 ?

Title: Triflouromethyl group deactivating
Post by: psychokitty 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.