Bromine → 6-Bromo-5-fluoroindoline
反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[Br:11]Br>OS(O)(=O)=O.S([O-])([O-])(=O)=O.[Ag+2]>[Br:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][NH:7]2)=[CH:3][C:2]=1[F:1]参加物
5
反応条件
- 温度
- -5 °C
実験手順
A solution of 5-fluoroindoline (4.65 g, 34 mmole) in conc. H2SO4 acid (60 ml) under argon was treated with silver sulfate (5.5 g, 18 mmole) and stirred for 0.5 h, then cooled to −5° C. and treated dropwise over 15 min with bromine (5.6 g, 35 mmole). The mixture was maintained at −5° C. for 0.5 h, then allowed to warm to room temperature over 1 h, before adding cautiously to well stirred ice/water (600 ml). The mixture was filtered through Kieselguhr, then basified by addition of 40% NaOH solution and extracted with Et2O (2×300 ml). The combined extract was dried (Na2SO4) and concentrated under vacuum to afford the title compound as a beige solid (6.5 g, 89%). MH+ 216/218.