Allyl bromide → 5-(prop-2-en-1-yloxy)-1H-indole

Participants

Reaction Steps

To a slurry of 2.92 g (22 mmol) 5-hydroxyindole and 12.43 g (90 mmol) K2CO3 in 110 mL acetone was added 2.07 mL (24 mmol) allyl bromide. The reaction was stirred at room temperature over 2 days upon which time TLC indicated that the reaction was not complete. Additional 0.66 mL allyl bromide was added and the reaction was heated to reflux for 1.5 hr and stirred at room temperature over night. The reaction was filtered to remove precipitate and concentrated. The crude product was chromatographed on silica gel using 20–33% EtOAc-hexane to afford 3.128 g (18 mmol) 5-allyloxyindole as an oil.

Provenance & Evidence