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-7ace36923b6b403d9f40affaf86db5aa

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06455525B1