Hydrochloric Acid → 5,6-Difluoro-1h-indole-3-carbaldehyde

To a solution of 5,6-difluoro-1H-indole (1.0 g) in N,N-dimethylformamide (10 mL) was added phosphoryl chloride (1.2 g) at 0° C., and this mixture was stirred at room temperature for 4 hours. To this mixture was added 2 mol/L aqueous sodium hydroxide solution (5 mL), and this resulting mixture was stirred at 70° C. for 0.5 hours. After cooling to ambient temperature, this mixture was poured into 1 mol/L hydrochloric acid and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (1.1 g).

1. stirringthis resulting mixture was stirred at 70° C. for 0.5 hours
2. temperatureAfter cooling to ambient temperature
3. extractionthe resulting mixture was extracted with ethyl acetate
4. washThe organic layer was washed with water and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was removed under reduced pressure

ORD record

ord-f9da1df7f52d4e85aa1f8cf979f286cc

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993616B2