Bromine → HCID 66788818, compound

Participants

Reaction Conditions

Reaction Steps

Water (14 mL) was added to 4-cyclopropyl-1-methyl-1,3-dihydro-indol-2-one (0.74 g, 3.94 mmol) and the resulting mixture was placed at 70° C. In a separate flask potassium bromide (1.03 g, 8.7 mmol) in water (14 was treated with bromine (0.225 mL, 4.3 mmol), the resulting orange solution was added dropwise to the 4-cyclopropyl-1-methyl-1,3-dihydro-indol-2-one mixture over ca. 10 minutes. The resulting heterogeneous mixture was permitted to stir at 70° C. for an additional hour and then cooled to room temperature. The reaction was then diluted with dichloromethane and saturated aqueous sodium bicarbonate. The solution was then further diluted with saturated aqueous sodium thiosulfate. The layers were separated and the aqueous layer eras extracted two additional times with dichloromethane. The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was preadsorbed onto silica gel and purified by silica gel flash chromatography (ethyl acetate-heptane 0 to 50%) to provide 5-bromo-4-cyclopropyl-1-methyl-1,3-dihydro-indol-2-one; MS: (ES+) m/z 266.2 (M+H)+.

Provenance & Evidence