Methyl iodide → 6-Chloro-1-methyl-1H-indole

Participants

Reaction Steps

A mixture of 6-chloroindole (22.0 g, 0.145 mole) and potassium t-butoxide (KOt-Bu) (20.0 g 0.179 mole) in tetrahydrofuran at room temperature is treated dropwise with methyl iodide (11.2 mL, 0.179 mole), allowed to stir at ambient temperatures for about 1 hour and diluted with a mixture of pet ether and water. The phases are separated. The organic phase is washed with 1 N HCL and water, dried over Na2SO4 and concentrated to a brown oil. After chromatography (silica gel/4:1 hexanes:ethyl acetate), the oil is distilled to afford the title product as a colorless oil, 16.25 g (67% yield), bp 110°-115° C./4 mm Hg, identified by IR, 1HNMR, 13CNMR, mass spectral and microanalyses.

Provenance & Evidence