Sign up for free shipping on all website orders, no minimum required, and get exclusive coupons!
TCI offers bulk solutions for a wide range of chemical reagents. Get a Quote for Your Bulk Chemical Requirements.
Maximum quantity allowed is 999
Please select the quantity
TCI Practical Example: Formylation of Aromatic Compound Using the Vilsmeier Reagent
We are proud to present the formylation of indole using the Vilsmeier reagent.
Used Chemicals
Procedure
- 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 the solution was stirred for 2.5 hours at room temperature. The reaction mixture was quenched with 1 mol/L NaOH aq. (13 mL) and diluted with water (12 mL). The solution was poured into ice-cooled water (25 mL) and stirred for 1 hour at the same temperature. The precipitation was collected by filtration, washed with water (3 x 3 mL), and dried under reduced pressure to give indole-3-carbaldehyde as a pale yellow solid (529 mg, 77% yield).
Experimenter's Comments
The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:1, Rf = 0.32).
Since Vilsmeier reagent has hydroscopicity, it was quickly weighed and used.
Analytical Data
Indole-3-carboxaldehyde
1H NMR (270 MHz, DMSO-d6); δ 12.11 (brs, 1H), 9.94 (s, 1H), 8.27 (s, 1H), 8.09 (d, J = 7.6 Hz, 1H), 7.51 (d, J = 7.8 Hz, 1H), 7.29-7.19 (m, 2H).
Other Reference
- Discovery and synthesis of novel indole derivatives-containing 3-methylenedihydrofuran-2(3H)-one as irreversible LSD1 inhibitors
