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-2780a6ee9ec14ef08fe88f31cb120d5d

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003647B2