Hydrochloric Acid → (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-6-fluoro-1,3-dihydro-2H-indol-2-one

Temperature

0 °C

To a solution of 6-fluorooxindole (3 g, 20 mmol) in THF (50 mL) at 0° C., was added 40 mL of 1M LHMDS in THF. The reaction mixture was stirred at 0° C. for 15 minutes. A solution of 4-bromo-5, 5-dimethyl-5H-furan-2-one (5) (1.91 g, 10 mmol) in 5 mL of THF was added to the above reaction mixture. The reaction was stirred at 0° C. for further 30 minutes and then at room temperature for 2.5 hrs. To the reaction, 80 mL of 2M HCl was added. The resulting mixture was stirred at 50-55° C. for one hour, cooled down to room temperature, poured to 1000 mL of water and was stirred at room temperature for one hour. The precipitates formed were collected and washed with water, dried in vacuum to give the title compound as a yellow solid product (2.4 g, yield: 74%).

1. stirringThe reaction was stirred at 0° C. for further 30 minutes
2. waitat room temperature for 2.5 hrs
3. additionwas added
4. stirringThe resulting mixture was stirred at 50-55° C. for one hour
5. temperaturecooled down to room temperature
6. stirringwas stirred at room temperature for one hour
7. customThe precipitates formed
8. customwere collected
9. washwashed with water
10. customdried in vacuum

ORD record

ord-83ac01274e974ca5a0079bccd05b3499

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367664B2