Bromine → HCID 66788022, compound

Temperature

68 °C

Water (25 mL) was added to 4-chloro-1-methyl-1,3-dihydro-indol-2-one (1.25 g, 6.9 mmol) and the resulting mixture was placed at 68° C. In a separate flask potassium bromide (1.64 g, 13.8 mmol) in water (25 mL) was treated with bromine (0.35 mL, 6.9 mmol), the resulting orange solution was added dropwise to the 4-chloro-1-methyl-1,3-dihydro-indol-2-one mixture over ca. 20 minutes. The resulting heterogeneous mixture was permitted to stir at 68° C. for an additional 5 minutes 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 was 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 15 to 50%) to provide 5-bromo-4-chloro-1-methyl-1,3-dihydro-indol-2-one; MS: (ES+) m/z 259.9 (M+H)+.

1. customwas placed at 68° C
2. temperaturecooled to room temperature
3. customThe layers were separated
4. extractionthe aqueous layer was extracted two additional times with dichloromethane
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. custompurified by silica gel flash chromatography (ethyl acetate-heptane 15 to 50%)

ORD record

ord-d2ee6e64bf1840269faa82f0620f711b

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778972B2