Potassium Iodide → 6-Methyl-4-iodo-indole-3-carboxaldehyde

Temperature

30 °C

A solution of thallium (III) trifluoroacetate (1 g, 1.84 mmol) in trifluoroacetic acid (15 mL) was added to 6-methyl-indole-3-carboxaldehyde (200 mg, 1.25 mmol) and the resulting mixture was stirred at 30° C. for 2 h. The solvent was removed under vacuum (rotary evaporator). To the residue was added an aqueous solution of potassium iodide (2 g, 12 mmol, in 20 mL of water) and the mixture was stirred at room temperature overnight. Solid sodium meta-bisulfite was added to the reaction mixture until it turned yellow. The mixture was basified with aqueous NaOH solution and was extracted repeatedly from diethyl ether. The combined organic was washed with brine and was dried over magnesium sulfate. Evaporation of solvent gave the crude product, which was purified by flash chromatography by using EtOAc as eluent. The product, 6-methyl-4-iodo-indole-3-carboxaldehyde was isolated as solid to yield 283 mg (79%) of the desired product. MS: 286.

1. customThe solvent was removed under vacuum (rotary evaporator)
2. stirringthe mixture was stirred at room temperature overnight
3. extractionwas extracted repeatedly from diethyl ether
4. washThe combined organic was washed with brine
5. dry with materialwas dried over magnesium sulfate
6. customEvaporation of solvent
7. customgave the crude product, which
8. customwas purified by flash chromatography

ORD record

ord-d7eedb42930d4f6e80b9855dd268351a

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06831075B2