Nemo_Tenetur (Newbee)
05-12-02 11:00
No 307685
      Benzotrifluoride acylation?  Bookmark   

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
()
05-14-02 11:36
No 308459
      Triflouromethyl group deactivating  Bookmark   

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.