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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: lutesium on April 26, 2008, 09:05:48 PM

Title: POCl3 use as an acylating reagent
Post by: lutesium on April 26, 2008, 09:05:48 PM

Dear Sir/Ma'am

I have a paper at which it shows a Carboxylic Acid + Amine forming an amide by the addition of POCl3!!! There must be an Acyl Halide intermediate right??? So here's my question:

Can POCl3 be used as an acylating reagent???


Lutesium...

Title: Re: POCl3 use as an acylating reagent
Post by: macman104 on April 26, 2008, 11:54:30 PM

I believe POCl3 will form the acyl chloride, similar to the mechanism in the Vilsmeier-Haack Reaction (http://en.wikipedia.org/wiki/Vilsmeier-Haack_reaction#Reaction_mechanism)

Title: Re: POCl3 use as an acylating reagent
Post by: g-bones on April 27, 2008, 02:44:51 AM

Quote from: macman104 on April 26, 2008, 11:54:30 PM

I believe POCl3 will form the acyl chloride, similar to the mechanism in the Vilsmeier-Haack Reaction (http://en.wikipedia.org/wiki/Vilsmeier-Haack_reaction#Reaction_mechanism)

Are you thinking of PCl3? this will turn a carboxylic acid to an acid chloride, like SOCl2

Title: Re: POCl3 use as an acylating reagent
Post by: macman104 on April 27, 2008, 04:36:10 AM

No, but similar to vilsmeier-haack which turns a amide into a intermediate chloride.