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Halogenation of a carboxylic acid using SO2Cl2
Meter:
Hi.
I found this step in a synthesis of a certain compound and I determined that it looks a lot like the chlorination of a carboxylic acid. From what I can find, such chlorinations generally use SOCl2 (thionyl chloride) and not SO2Cl2 (sulfuryl chloride). What makes this different?
rolnor:
It looks strange, DMF can probably not be the solvent? Maybe its a type-error, it should be SOCl2? Also you will get the product as HCl-salt.
Meter:
--- Quote from: rolnor on January 18, 2021, 03:10:01 AM ---It looks strange, DMF can probably not be the solvent? Maybe its a type-error, it should be SOCl2? Also you will get the product as HCl-salt.
--- End quote ---
I just realized that the article in which I found the synthesis, they do not cite a source for its synthesis pathway. Wikipedia isn't always a great source, so it could just be nonsense.
AWK:
If this diagram is from Wikipedia, there is sure to be a link citing the original publication there. Printing errors can happen anywhere.
Once you notice an error, you can correct it yourself after thoroughly checking the reference literature.
DMF is commonly used as a catalyst in the synthesis of acid chlorides with thionyl chloride.
rolnor:
I think DMF is used as catalyst when oxalyl chloride is used, not thionyl chloride. It is not used as solvent?
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