反应详情

温度

-70 °C

Under an argon stream, 1-bromo-4-tert-butylbenzene (125 g, 587 mmol) and tetrahydrofuran (470 mL) were charged in a reactor, and cooled to −70° C. An n-butyl lithium/hexane solution (1.6 M, 367 mL, 587 mmol) was dropped to this solution over 90 minutes at −70° C. After dropping was completed, the solution was stirred at −70° C. for 2 hours to obtain a 4-tert-butylphenyllithium/THF solution. Under an argon stream, cyanuric chloride (50.8 g, 276 mmol) and tetrahydrofuran (463 mL) were charged in another reactor, and cooled to −70° C. The 4-tert-butylphenyllithium/THF solution prepared previously was slowly dropped to this solution while the solution was cooled so that the reaction temperature might be not more than −60° C. After dropping was completed, the reaction solution was stirred at −40° C. for 4 hours, and stirred at room temperature for 4 hours. Water (50 mL) was added to this reaction mixture to complete the reaction, and tetrahydrofuran was distilled off. Water (1 L) and chloroform (2 L) were added to this residue, and an organic layer was extracted. The organic layer was further washed with water (1 L), and subsequently the solvent was distilled off. This residue was dissolved in acetonitrile (600 mL), and an insoluble solid was removed by filtration at the time of heating. The obtained filtrate was condensed to approximately 100 mL, and cooled to −70° C. to filter and collect the solid deposited. The collected solid was dissolved in a mixed solvent of chloroform (200 mL)/hexane (600 mL), and purified with silica gel column chromatography (developing solvent: chloroform/hexane). The solvent was distilled off, and this residue was recrystallized from acetonitrile. Thereby, 4,6-bis(4′-tert-butylphenyl)-2-chloro-1,3,5-triazine (41.3 g, 109 mmol) was obtained.

1. additionwas slowly dropped to this solution while the solution
2. temperaturewas cooled so that the reaction temperature
3. custommight be not more than −60° C
4. stirringstirred at room temperature for 4 hours
5. distillationwas distilled off
6. additionWater (1 L) and chloroform (2 L) were added to this residue
7. extractionan organic layer was extracted
8. washThe organic layer was further washed with water (1 L)
9. distillationsubsequently the solvent was distilled off
10. dissolutionThis residue was dissolved in acetonitrile (600 mL)
11. customan insoluble solid was removed by filtration at the time
12. temperatureof heating
13. customcondensed to approximately 100 mL
14. temperaturecooled to −70° C.
15. filtrationto filter
16. customcollect the solid
17. dissolutionThe collected solid was dissolved in a mixed solvent of chloroform (200 mL)/hexane (600 mL)
18. custompurified with silica gel column chromatography (developing solvent: chloroform/hexane)
19. distillationThe solvent was distilled off
20. customthis residue was recrystallized from acetonitrile