تفاعل #748290

معادلة التفاعل

ethyl 2-(3-fluoro-2-nitrophenyl)acetate

→

7-fluoroindolin-2-one

المردود 58.0%

المذيبات

AcOH

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction mixture was concentrated
2. 2
   workup.DISSOLUTIONdissolved in 100 mL of EtOAc
3. 3
   ترشيحfiltered
4. 4
   غسيلwashed with 50 mL of a saturated NaHCO3 solution
5. 5
   تركيزThe organic layer was concentrated
6. 6
   أخرىpurified with silica gel column chromatography
7. 7
   غسيلeluting with 40% EtOAc/hexane

الإجراء التجريبي

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).

المصدر