Vilsmeier–Haack reaction

The Vilsmeier–Haack reaction is the chemical reaction of a substituted formamide with phosphorus oxychloride and an electron-rich arene to produce an aryl aldehyde or ketone :
The reaction is named after Anton Vilsmeier and.
For example, benzanilide and dimethylaniline react with phosphorus oxychloride to produce an unsymmetrical diaryl ketone. Similarly, anthracene is formylated at the 9-position. The reaction of anthracene with N-methylformanilide, also using phosphorus oxychloride, gives 9-anthracenecarboxaldehyde:
In general, the electron-rich arene must be much more active than benzene for the reaction to proceed; phenols or anilines are good substrates.

Reaction mechanism

The reaction of a substituted amide with phosphorus oxychloride gives a substituted chloroiminium ion, also called the Vilsmeier reagent. The initial product is an iminium ion, which is hydrolyzed to the corresponding ketone or aldehyde during workup.