| 80% |
|
Sodium hydride (20 mmol, 0.7 g, 2 eq) is added slowly to a solution of carbazole (10 mmol, 1.7 g, 1 eq) in anhydrous tetrahydrofuran (approximately 30 mL) at ambient temperature. It is noted that a gas is given off (release of H2) and the solution changes colour from yellow to off-white. The mixture is left under stirring at ambient temperature for one hour, when the solution becomes light brown. Benzyl bromide (1.8 mL, 1.5 eq) is added dropwise to the mixture under stirring at ambient temperature. The mixture is left under stirring for approximately 3 hours and TLCs are carried out to verify if the reaction has finished. At the end of the reaction, water is added to the reaction mixture which is extracted with diethyl ether. The collected organic phases were dried with MgSO4 and the solvent is then evaporated. The solid obtained is washed with n-hexane. The product is obtained in the form of a white solid that is not very dense. Yield 80% |
| 78% |
|
General procedure: KOH (7 g, 125 mmol) was dissolved in acetone (15 mL) and the resulting solution was stirred at room temperature for 30 min. Carbazole (3.3 g, 20 mmol) was then added and reacted for 4 h. The acetone (15 mL) containing appropriate benzyl bromide (30 mmol) was added into the above solution and the resulting system was allowed to react overnight. When the reaction mixture was poured into water (250 mL), the solid was filtrated. After recrystallization from ethanol, a white solid was obtained in 53-84% yields5. |
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To a mixture of carbazole (0.87 g, 5 mmoles) in tetrahydrofuran (THF), NaH (0.24 g, 10 mmoles) was slowly added. The mixture was stirred for 1 hour, obtaining a solution. Benzyl bromide (0.89 ml, 7.5 mmoles) was then added dropwise, and the reaction mixture was stirred for 5 hours at room temperature. The reaction was quenched with ice water and THF was evaporated under reduced pressure. The mixture was extracted with ethyl ether (3 x 5 mL) and the organic phases were collected and combined, dried over MgSO4 and evaporated under reduced pressure. The solid obtained was triturated with n-hexane (10 mL), filtered and used without further purification. The compound obtained is a white solid with melting point of 123C and Rf = 0.44 in cyclohexane/dichloromethane 4/ 1.IH-NMR (CDCl3, 300 MHz) delta: 8. 14 (d, 2H, J = 7.5 Hz); 7.74-7.14 (m, HH); 5.54 (s, 2H). |
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With NaH; In tetrahydrofuran; |
9-benzyl-carbazole To a mixture of carbazole (0.87 g, 5 mmoles) in tetrahydrofuran (THF), NaH (0.24 g, 10 mmoles) was slowly added. The mixture was stirred for 1 hour, obtaining a solution. Benzyl bromide (0.89 ml, 7.5 mmoles) was then added dropwise, and the reaction mixture was stirred for 5 hours at room temperature. The reaction was quenched with ice water and THF was evaporated under reduced pressure. The mixture was extracted with ethyl ether (3*5 mL) and the organic phases were collected and combined, dried over MgSO4 and evaporated under reduced pressure. The solid obtained was triturated with n-hexane (10 mL), filtered and used without further purification. The compound obtained is a white solid with melting point of 123 C. and Rf=0.44 in cyclohexane/dichloromethane 4/1. 1H-NMR (CDCl3, 300 MHz) delta: 8.14 (d, 2H, J=7.5 Hz); 7.74-7.14 (m, 11H); 5.54 (s, 2H). |
| 3.56 g |
With cetyltrimethylammonim bromide; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 12.75h; |
In a 100mL three-necked flask equipped with a magnetic stirrer, 2.8g (50mmol) KOH and 50mL DMF was successively added. After stirring for 15min, 4.18g (25mmol) carbazole and 0.05g (0.15mmol) CTAB was added and stirring was continued for 30min. From the pressure-equalizing dropping funnel, 1.66g (35mmol) of benzylbromide was slowly added dropwise. The reaction was continued at room temperature for 12h. Cooling to room temperature, the reaction mixture was poured into 100mL of deionized water and was filtered to form a white precipitate. This was rinsed with deionized water three times, drained, and dried under reduced pressure to form white flaky crystals. The residue was recrytallized from absolute ethanol and dried giving 3.56g of N-benzylcarbazole as a white crystalline solid. |
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With tetra-(n-butyl)ammonium iodide; potassium hydroxide; In water; toluene;Reflux; |
Into a 100 mL one-necked round bottom flask were added carbazole (4.3 g, 17.9 mmol), benzylbromide (2.56 g, 15.0 mmol), tetrabutylammonium iodide (0.55 g, 0.15 mmol), 50 wt% of aqueousKOH solution (30 mL) and toluene (30 mL). The reaction mixture was heated to reflux overnight.After cooling to room temperature, the reaction mixture was extracted with toluene. The organiclayer was washed with water and dried over magnesium sulfate. A white solid was obtained in88% yield (3.39 g) and used without any further purification. |
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With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 8h;Inert atmosphere; |
Add 0.3 g (1.8 mmol) of carbazole and 0.7 g (2.16 mmol) of cesium carbonate to a two-necked flask, draw it out, and inject 40 ml of anhydrous dimethylformamide;0.235 ml (1.98 mmol) of benzyl bromide and 20 ml of anhydrous dimethylformamide (DMF) were added to a constant pressure funnel;Under the protection of argon gas, the liquid in the constant pressure funnel was slowly added dropwise to the double-necked flask, and the reaction was performed at room temperature for 8 hours.After the reaction was completed, the organic phase was extracted with dichloromethane, washed with water with shaking, anhydrous magnesium sulfate was added to remove water, filtered, spin-dried, and separated by silica gel column chromatography to obtain N-benzylcarbazole. |
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