Also known as: Vilsmeier-Haack formylation

Schematic of the Vilsmeier-Haack reaction. Reagents: electron rich carbocycle, DMF, acid chloride (POCl3), aqueous work-up. Product: aryl aldehyde.

The Vilsmeier-Haack reaction is an organic reaction used to convert an electron rich aromatic ring to an aryl aldehyde using 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”. Price of 3-Iodo-4-(trifluoromethyl)aniline 213125-87-2 Chemical name The electron rich aromatic ring then attacks the iminium ion with loss of aromaticity. A deprotonation step restores aromati-city, which is followed by the release of a chloride ion to form another iminium intermediate. Aqueous work-up then leads to the aryl aldehyde final product. [1]

Mechanism

Mechanism of the Vilsmeier-Haack reaction. Vilsmeier reagent.

References:

1.
Vilsmeier, A.; Haack, A. Ber. dtsch. Chem. Ges. 1927, 60, 119–122.