Methyl iodide → 4-Fluoro-1-methyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

In DMF (40 ml) was dissolved 4-fluoroindole (2.00 g, 14.8 mmol). To the resulting solution was added sodium hydride (60% in oil, 0.71 g, 17.8 mmol) in portions under stirring at 0° C. After the reaction mixture was stirred for 40 minutes at the same temperature, methyl iodide (1.11 ml, 17.8 mmol) was added at 0° C. The reaction mixture was stirred further at the same temperature for 4 hours. A saturated aqueous solution of ammonium chloride was added to terminate the reaction. The reaction mixture was extracted with ether, and the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (5:1, v/v) eluate fractions, 4-fluoro-1-methylindole (2.20 g, 100%) was obtained as a yellow oil.

Provenance & Evidence