Methyl iodide → 5-Bromo-1-methyl-1H-indole

Participants

Reaction Steps

A solution of 5-bromo-1H-indole (1.530 mmol) in dimethyl sulfoxide (10 mL) was treated with NaOH (2.295 mmol) and stirred at room temperature for 30 min. The solution was then treated with methyl iodide (4.59 mmol) and was stirred for 3 days at room temperature. The solution was diluted with water (100 mL) and was extracted with ethyl acetate. The combined organic phases were washed with water, washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The yellow oil was used without further purification. MS(ES)+ m/e 210/212 [M+H]+ (bromide isotope pattern).

Provenance & Evidence