IIT JAM UGC CSIR NET GATE CHEMISTRY

    PDF || Vilsmeyer Haack Reaction

    at a glance :

    The Vilsmeier-Haack reaction is an organic reaction used to convert an electron rich aromatic ring to an aryl aldehyde by thge treatment with DMF, an acid chloride, and aqueous work-up. The mechanism begins with the reaction of DMF with the acid chloride to form an iminium salt known as the "Vilsmeier reagent''.

    

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     DMF:  

    Dimethylformamide is an organic compound with the formula C3H7NO. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran or dimethyl fumarate, this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. 

    

       Vilsmeier Reagent : 

Vilsmeier reagent is the active intermediate in the formylation reactions. The Vilsmeier-Haack reaction that use mixtures of dimethylformamide and phosphorus oxychloride to generate the Vilsmeier reagent, which in turn attacks a nucleophilic substrate and eventually hydrolyzes to give formyl.