Ethyl 2-(3-fluoro-2-nitrophenyl)acetate → 7-Fluoro-2,3-dihydro-1h-indol-2-one

Temperature

60 °C

To a 250 mL round bottom flask was added ethyl 2-(3-fluoro-2-nitrophenyl)acetate (3.1 g, 14 mmol), iron (3.8 g, 68 mmol), and 50 mL of AcOH. The reaction mixture was heated at 60° C. for 1 hour. The reaction mixture was concentrated and dissolved in 100 mL of EtOAc, filtered, and washed with 50 mL of a saturated NaHCO3 solution. The organic layer was concentrated and purified with silica gel column chromatography, eluting with 40% EtOAc/hexane to give 7-fluoroindolin-2-one (1.2 g, 58% yield) as a white solid. MS m/z: 152 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 3.58 (s, 2H), 6.94-7.04 (m, 3H).

1. concentrationThe reaction mixture was concentrated
2. dissolutiondissolved in 100 mL of EtOAc
3. filtrationfiltered
4. washwashed with 50 mL of a saturated NaHCO3 solution
5. concentrationThe organic layer was concentrated
6. custompurified with silica gel column chromatography
7. washeluting with 40% EtOAc/hexane

ORD record

ord-008c352e667a4a35a82745b6f89e863d

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084479B2