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Author: Subject: 3',4',5'-trichloro-2,2,2-trifluoroacetophenone
hmtlion
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[*] posted on 4-1-2013 at 01:17
3',4',5'-trichloro-2,2,2-trifluoroacetophenone


Dear All

I wish to make 3',4',5'-trichloro-2,2,2-trifluoroacetophenone for my research work.

did any one made this compound?

Please provide all information

Regards
Hardik
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kavu
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[*] posted on 4-1-2013 at 01:39


This patent describes one possible synthesis: WO2012120135

They lithanate 5-bromo-1,2,3-trichlorobenzene and toss in ethyl trifluoroacetate.

[Edited on 4-1-2013 by kavu]
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kristofvagyok
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[*] posted on 4-1-2013 at 09:47


Quote: Originally posted by kavu  
This patent describes one possible synthesis: WO2012120135

They lithanate 5-bromo-1,2,3-trichlorobenzene and toss in ethyl trifluoroacetate.


Important to note for that they used some n-BuLi for the metallation of the trichlorobromobenzene what is not the best to work with.

I would suggest to use a Grignard instead of the BuLi, much better to work with...

If 3,4,5 trichlorobenzaldehyde is aviable than there is also another route, with trifluormethyl-iodide or bromide, a schlenk tube and some zinc powder. It will form the corresponding alcohol what could be easily oxidized to the ketone.
This is described at: Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990 , # 7 p. 1951 - 1957
Another version: Chemistry Letters, 1984 , p. 517 - 520

Also there is another version of this reaction where they generate the trifluormethyliodide in situ from sodium trifluoracetate: Journal of Fluorine Chemistry, 2005 , vol. 126, # 6 p. 937 - 940




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hmtlion
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[*] posted on 6-1-2013 at 21:00


Thanks
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VitaminX
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[*] posted on 10-1-2013 at 17:47


I synthesized 2',2',2'-Trichloro and 2',2',2'-Trifluoroacetophenone (without ring substitution) and I have to warn you. It is a VERY strong lachrimatory. I wanted to die right there right now.

It was synthed from acetophenone with Cl2 gas. Synthesis was performed from: Cohen S., Wolosinski H., Scheurer P., J. Am. Chem. Soc., 72, 3952,1950

If you start from the 3,4,5-trichloroacetophenone you should get what you need.

[Edited on 11-1-2013 by VitaminX]
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hmtlion
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[*] posted on 29-1-2013 at 23:10
Thnaks


Thnaks, I got the compound. via grignard
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[*] posted on 31-1-2013 at 22:45


did any one made this compound?
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