Vilsmeier Reagent for Formylation of Aromatic Compounds

Vilsmeier Reagent [C1545] is used for the formylation of aromatic compounds, introducing a formyl group onto the aromatic ring. In the example highlighted by TCI, indole (500 mg, 4.27 mmol) was added to a solution of Vilsmeier Reagent (1.09 g, 8.54 mmol, 2.0 eq.) in DMF (8.5 mL) at 0 °C and stirred for 2.5 hours at room temperature. After quenching with 1 mol/L NaOH aq. and dilution with water, the mixture was poured into ice-cooled water, stirred for 1 hour, and the precipitate was collected by filtration. This procedure gave indole-3-carbaldehyde as a pale yellow solid (529 mg, 77% yield). The reaction was monitored by TLC (ethyl acetate:hexane = 1:1, Rf = 0.32). Because the reagent is hygroscopic, TCI notes that it should be weighed quickly and used promptly.

Related products

• TCI C1545 3724-43-4 (Chloromethylene)dimethyliminium Chloride
• TCI I0021 120-72-9 Indole

Source

• TCI Practical Example: www.tcichemicals.com/ID/en/product/tci-topics/TCIPracticalExample_20250421
• TCI product page C1545: tcichemicals.com/ID/en/p/C1545

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