The Vilsmeier reagent is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula CH₃)₂NCHCll. It is a salt consisting of the N,N-dimethyliminium cation ( CH₃)₂N=CHClsup>+) and chloride anion. Depending on the particular reaction, the anion can vary. In typical POCl₃-based reactions, the anion is PO₂Cl₂⁻. The iminium cation CH₃)₂N=CHClsup>+ is the reactive component of interest. This iminium species is a derivative of the imidoyl chloride CH₃N=CHCl. Analogues of this particular reagent are generated when tertiary amides other than DMF are treated with POCl₃. The salt is a white solid that is soluble in polar organic solvents. Vilsmeier reagent is the active intermediate in the formylation reactions, the Vilsmeier reaction or Vilsmeier-Haack reaction that use mixtures of

dimethylformamide Dimethylformamide, DMF is an organic compound with the chemical formula . Its structure is . Commonly abbreviated as DMF (although this initialism is sometimes used for 2,5-dimethylfuran, dimethylfuran, or dimethyl fumarate), this colourless liqui ...

and

phosphorus oxychloride Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula . It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phos ...

to generate the Vilsmeier reagent, which in turn attacks a nucleophilic substrate and eventually hydrolyzes to give formyl. It is a source of "O=CH⁺".

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References

Reagents

See also

References