反应详情

温度

70 °C

To a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)1H-indole (pinacole 4-indoleboronate (2 g, 8.2 mmol) and 3-bromobenzene (0.87 mL, 8.3 mmol) in THF (28 mL) were added Palladium catalyst Pd(PPh3)4 (284 mg, 0.25 mmol) and the freshly prepared sodium hydroxide solution (984 mg in 9 mL of water). The system was degassed and then charged with nitrogen for three times. The mixture was stirred under nitrogen at 70° C. oil bath for 6 hours. The reaction solution was cooled to room temperature, diluted with ethyl acetate and separated from water layer. The ethyl acetate solution was washed by brine, dried over Na2SO4 and concentrated. The residue was purified on a silica gel column eluting with hexanes:EtOAc 9:1 to give 1.38 g (78%) of 4-phenyl-1H-indole as a colorless liquid.

1. customThe system was degassed
2. additioncharged with nitrogen for three times
3. temperatureThe reaction solution was cooled to room temperature
4. additiondiluted with ethyl acetate
5. customseparated from water layer
6. washThe ethyl acetate solution was washed by brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customThe residue was purified on a silica gel column
10. washeluting with hexanes:EtOAc 9:1