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Halogenation of a carboxylic acid using SO2Cl2
Meter:
--- Quote from: AWK on January 18, 2021, 06:37:01 AM ---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.
--- End quote ---
It doesn't seem like there is a paper attached to it.
Babcock_Hall:
A slightly tangential comment: It has been some time since I worked with SO2Cl2, but I used to distill it away from a lower boiling impurity shortly before use.
wildfyr:
DMF is perfectly fine to be a solvent. Why wouldn't it be? I'm more concerned about that amine there either reacting with the acid chloride or this thing precipitating out when protonated.
BTW its common to run chlorinations in neat thionyl chloride, sometimes with a drop of catalytic DMF.
Workup is either distill off thionyl chloride, or if the product is kinda water stable, dump it into ice then extract with water and organic solvent.
rolnor:
Wildfyr, I think acid chlorides react with DMF much like POCl3 does when you make Wilsmeyers reagent.
I have never seen DMF used as catalyst when making acid chlorides with SOCl2 but often when oxalyl chloride is used.
wildfyr:
Hm... I think i've used those conditions for SO3Na --->SO2Cl
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