Acetic Acid → HCID 22561931, compound

Participants

Reaction Steps

To the suspension of 5-methoxyindole (5.0 g, 34 mmol) in t-BuOH: ethanol: acetic acid (215 mL: 127 mL: 66 mL) was added pyridinium tribromide (32.6 g, 102 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added with more acetic acid (165 mL). Zinc dust (11.1 g, 170 mmol) was added to the reaction mixture portionwise. After stirring for one hour, the unreacted zinc was filtered off, and the solvent was removed under reduced pressure. The residue was diluted with water, extracted with ethyl acetate. The combined extracts were washed with water (5×), sat. NaHCO3 (2×), brine (3×), dried over Na2SO4, concentrated, triturated with ether to give 2.12 g (26%) of 4-bromo-5-methoxy-1,3-dihydro-indol-2-one.

Provenance & Evidence