反应详情

温度

-78 °C

A 2 L dry round bottom flask was charged with N-benzyl-3,6-dibromocarbazole 3 (49 g, 0.118 mol) and 1 L of dry THF was added. The mixture was stirred until N-benzyl-3,6-dibromocarbazole 3 was dissolved. The mixture was then cooled to −78° C. and 2.5 M n-BuLi in hexanes (104 ml, 0.26 mol) was added dropwise. The mixture was stirred at −78° C. for 15 min and triisopropylsilyl-trifluoromethyl sulfonate (66 ml, 0.26 mol) was added. The mixture was left to warm up to room temperature overnight. The mixture was then quenched with sat. NH4Cl, extracted with methyl-t-butyl ether, dried over Na2SO4, filtered, concentrated, and purified over a 330 g SiO2 column to yield 9-benzyl-3,6-bis-triisopropylsilanyl-9H-carbazole 4 23.0 g (35%) as a transparent oil.

1. customA 2 L dry round bottom flask
2. additionwas added
3. dissolutionwas dissolved
4. waitThe mixture was left
5. temperatureto warm up to room temperature overnight
6. customThe mixture was then quenched with sat. NH4Cl
7. extractionextracted with methyl-t-butyl ether
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. custompurified over a 330 g SiO2 column