تفاعل #2360688

معادلة التفاعل

1-pyreneboronic acid

2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine

NaOH

→

2-[3,5-di(1-pyrenyl)-phenyl]-4,6-diphenyl-1,3,5-triazine

المردود 81.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىwas elevated to 70° C
2. 2
   workup.DISTILLATIONthe obtained mixture was distilled
3. 3
   درجة الحرارةunder reflux for 3 hours
4. 4
   أخرىThe resultant reaction mixture
5. 5
   workup.WAITwas left
6. 6
   أخرىto stand to room temperature
7. 7
   workup.DISTILLATIONdistilled under a reduced pressure
8. 8
   أخرىto remove all volatile materials
9. 9
   workup.ADDITIONMethanol was added to the concentrate
10. 10
    ترشيحthe thus-deposited solid was collected by filtration
11. 11
    أخرىThe thus-obtained crude product
12. 12
    أخرىwas recrystallized from o-xylene

الإجراء التجريبي

In a stream of argon, 1.26 g (5.13 mmol) of 1-pyreneboronic acid, 1.00 g (2.14 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 60.1 mg (0.081 mmol) of dichlorobis(triphenylphosphine)palladium were suspended in 75 mL of tetrahydrofuran, and the temperature of the obtained suspension was elevated to 70° C. 4.01 mL (16.1 mmol) of an aqueous 4N NaOH solution was gradually added dropwise to the suspension, and the obtained mixture was distilled under reflux for 3 hours. The resultant reaction mixture was left to stand to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The thus-obtained crude product was recrystallized from o-xylene to give 1.23 g of the target 2-[3,5-di(1-pyrenyl)-phenyl]-4,6-diphenyl-1,3,5-triazine as grayish white solid (yield: 81%).

المصدر