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Vilsmeier–Haack reaction

Chemical reaction

Summary

Chemical reaction

Albrecht Haack The Vilsmeier–Haack reaction (also called the Vilsmeier reaction) is the chemical reaction of a substituted formamide (1) with phosphorus oxychloride and an electron-rich arene (3) to produce an aryl aldehyde or ketone (5): : HArZ + POCl3 + H2O → RC(=O)ArZ + HCl + H3PO4 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:

:[[Image:Vilsmeier reaction example2.svg|thumb|650px|none|N-Methylformanilide and anthracene and phosphorus oxychloride]]

In general, the electron-rich arene (3) 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 (2), also called the Vilsmeier reagent. The initial product is an iminium ion (4b), which is hydrolyzed to the corresponding ketone or aldehyde during workup. :[[Image:Vilsmeier Haack Reaction Scheme.png|thumb|none|650px|The Vilsmeier–Haack reaction]]

References

References

  1. (1927). "Über die Einwirkung von Halogenphosphor auf Alkyl-formanilide. Eine neue Methode zur Darstellung sekundärer und tertiärer ''p''-Alkylamino-benzaldehyde". Berichte der Deutschen Chemischen Gesellschaft zu Berlin.
  2. (1991). "The Vilsmeier–Haack Reaction (Review)". Compr. Org. Synth..
  3. (1953). "Formylation of dimethylaniline".
  4. (1927). "Vilsmeyer–Haack reaction of benzanilide and dimethylaniline".
  5. (1940). "Formylation of anthracene".
  6. (2020). "March's Organic Chemistry". Wiley.
  7. (2000). "The Vilsmeier Reaction of Non-Aromatic Compounds". [[Org. React.]].
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