[AWK]

There is no mention of DMF, but the reaction concerns the preparation of acid chlorides and anhydrides by the action of SO₂ + Cl₂ on carboxylic acid salts, and the products may be acid chlorides or anhydrides depending on the proportion of reactants. The salts are wetted with ethyl acetate before reaction.

[rolnor]

I dont understand how this is relevant for the question from Meter?

[AWK]

It all started with the question (which is in the title of the thread) whether SO2Cl2 can be used to synthesize acid chlorides. Meter showed a reaction that also includes DMF (he claims the reaction is from Wikipedia).
You started a discussion about the advisability of using DMF, and then the discussion went sidetrack.

[rolnor]

Thats true. I think many reagents can be used to make acyl halides, including SO2Cl2. It looked as if they used DMF as solvent and that seems strange to me.

[wildfyr]

I've personally always used thionyl chloride, and its pretty much failsafe. Its more of a hassle to handle and get rid of than oxalyl chloride, but its also probably a more powerful chlorinating reagent. A "drop" of DMF was always suggested to me for making acyl chlorides or sulfonyl chlorides, but I never really compared with/without the DMF.

I've usually chlorinated in neat thionyl chloride, but sometimes done 1 eq in a solvent like DCM. When doing that I actually probably leave out the DMF. No accounting for my decision

[rolnor]

Yes thionyl chloride is good, for benzoic type acids reflux can be used, not nessecary with aliphatic acids I think.