Hydrogen Peroxide → HCID 11176292, compound

Temperature

50 °C

To crude methyl 3-[2-nitro-4-iodo-6-(trifluoromethyl)phenyl]-2-oxo-propanoate prepared above (40.98 g) in AcOH (750 mL) was added aqueous 30% H2O2 solution (266 mL) followed by 70% HClO4 (41 mL). The resulting mixture was stirred at 50° C. (bath temperature) for 4.5 hours. The solution was cooled and solid Na2SO3 (100 g) was added. The solvent was then removed in vacuo. The resulting orange solid was suspended in EtOAc (500 mL) and washed with H2O (300 mL). The organic phase was then extracted with aqueous saturated NaHCO3:aqueous 2N NaOH (6:1, 600 mL) followed by aqueous saturated NaHCO3 (200 mL). The aqueous extracts were combined and cooled in an ice-water bath. The solution was then acidified with aqueous 35% HCl. The resulting solid was isolated by filtration and dried to give the title compound as a yellow solid (7.086 g). The organic phase was then re-extracted with aqueous saturated NaHCO3 (6×50 mL). The extracts were combined and cooled in an ice-water bath, and then acidified with aqueous 35% HCl. The resulting solid was isolated by filtration and dried to give the title compound as a yellow solid (6.896 g).

1. temperatureThe solution was cooled
2. customThe solvent was then removed in vacuo
3. washwashed with H2O (300 mL)
4. extractionThe organic phase was then extracted with aqueous saturated NaHCO3
5. temperaturecooled in an ice-water bath
6. customThe resulting solid was isolated by filtration
7. customdried

ORD record

ord-b8428b949ddb4ace9364b788a28aa71c

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06576656B1