Ethyl 2-(5-bromo-4-fluoro-2-nitrophenyl)acetate → 5‐bromo‐6‐fluoro‐2,3‐dihydro‐1H‐indol‐2‐one
Reaktionsgleichung
[Br:1][C:2]1[C:3]([F:17])=[CH:4][C:5]([N+:14]([O-])=O)=[C:6]([CH2:8][C:9](OCC)=[O:10])[CH:7]=1>[Fe].CC(O)=O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[F:17])[NH:14][C:9](=[O:10])[CH2:8]2Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a 250 mL round bottom flask was added ethyl 2-(5-bromo-4-fluoro-2-nitrophenyl)acetate (5.2 g, 17 mmol), iron (4.7 g, 85 mmol) and 50 mL of AcOH. The reaction mixture was heated at 60° C. for 1 hour. The reaction mixture was then concentrated, 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 5-bromo-6-fluoroindolin-2-one (3.4 g, 87% yield) as a white solid. MS m/z: 230 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 3.49-3.54 (m, 2H), 6.77 (d, J=8.80 Hz, 1H), 7.45 (d, J=6.65 Hz, 1H).