Sodium Hydroxide → 6-bromo-1-isopropyl-1H-indole-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 2,2,2-trifluoro-1-(6-bromo-1-isopropyl-1H-indol-3-yl)-ethanone (3.30 g, 9.88 mmol) in a 20% aqueous sodium hydroxide solution (35 mL) was heated at 110° C. for 18 h. At this time, the reaction was cooled to 25° C., partitioned between water (100 mL) and ethyl acetate (100 mL), and treated with a 1N aqueous hydrochloric acid solution (60 mL). The organic layer was then washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 6-bromo-1-isopropyl-1H-indole-3-carboxylic acid (2.63 g, 94%) as a yellow solid: mp 207-209° C.; EI-HRMS m/e calcd for C12H12BrNO2 (M+) 281.0051, found 281.0047.

Provenance & Evidence