تفاعل #748291

معادلة التفاعل

Br2

KBr

7-Fluoroindolin-2-one

→

5-bromo-7-fluoroindolin-2-one

المردود 75.0%

المذيبات

water

water

ظروف التفاعل

المعالجة

1. 1
   أخرىto form as the solution
2. 2
   workup.ADDITIONwas added
3. 3
   درجة الحرارةThe mixture was then chilled in an ice bath for 30 minutes
4. 4
   غسيلwashed with 30 mL of a saturated NaHCO3 solution
5. 5
   استخلاصextracted twice with 50 mL of EtOAc
6. 6
   تركيزThe organic layers were concentrated
7. 7
   أخرىpurified with silica gel column chromatography
8. 8
   غسيلeluting with 0-35% EtOAc/hexane

الإجراء التجريبي

7-Fluoroindolin-2-one (800 mg, 5293 μmol) was taken up in 30 mL of boiling water. Br2 (273 μL, 5293 μmol) and KBr (1260 mg, 10586 μmol) were added dropwise in 5 mL of water over 10 minutes. A white precipitate began to form as the solution was added. The mixture was stirred for 20 minutes. The mixture was then chilled in an ice bath for 30 minutes, washed with 30 mL of a saturated NaHCO3 solution and extracted twice with 50 mL of EtOAc. The organic layers were concentrated and purified with silica gel column chromatography, eluting with 0-35% EtOAc/hexane to give 5-bromo-7-fluoroindolin-2-one (913 mg, 75% yield). MS m/z: 230 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 3.58 (s, 2H), 7.20 (dd, J=10.07, 0.88 Hz, 2H), 7.63 (s, 1H).

المصدر