反应详情

温度

-78 °C

In a stream of argon, tetrahydrofuran (3 mL) was cooled to −78° C. To the cooled tetrahydrofuran, a tetrahydrofuran solution (1.18 mL) of tert-butyllithium (1.58 mol/L) was added. Then a tetrahydrofuran solution (2 mL) of 2-bromo-6-phenylpyridine (211 mg) was dropwise added to the tert-butyllithium solution. The mixture was stirred for 15 minutes while the mixture was maintained at −78° C. To the reaction mixture, zinc chloride tetramethylethylenediamine complex (530 mg) was added to allow the temperature to rise naturally to room temperature. Then, to the reaction mixture, a tetrahydrofuran suspension (2 mL) having suspended therein 2,4-bis(5-bromobiphenyl-3-yl)-6-phenyl-1,3,5-triazine (185.8 mg) and tetrakis(triphenylphosphine)palladium (13.9 mg) was dropwise added. The resultant mixture was stirred at 50° C. for 19 hours. The reaction mixture was left to stand at room temperature, and then low-boiling ingredients were distilled away under a reduced pressure. Methanol was added, and the solid precipitate was recovered by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (2:1) mixed liquid as a developing solvent, to give 120 mg of the target 2,4-bis[5-(6-phenylpyridin-2-yl)biphenyl-3-yl]-6-phenyl-1,3,5-triazine as a white powder (yield: 52%).

1. additionTo the reaction mixture, zinc chloride tetramethylethylenediamine complex (530 mg) was added
2. customto rise naturally to room temperature
3. waitThe reaction mixture was left
4. customto stand at room temperature
5. distillationlow-boiling ingredients were distilled away under a reduced pressure
6. additionMethanol was added
7. filtrationthe solid precipitate was recovered by filtration
8. customThe obtained crude product
9. customwas purified by silica gel chromatography
10. additionmixed liquid as a developing solvent