تفاعل #2360674

معادلة التفاعل

1-pyreneboronic acid

4-(2-pyridyl)phenylboronic acid

K2CO3

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

→

4,6-diphenyl-2-[5-(1-pyrenyl)-4′-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine

المردود 26.0%

المذيبات

ethanol

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThen the mixture was heated to 70° C.
2. 2
   درجة الحرارةmaintained at that temperature for 3 hours
3. 3
   workup.STIRRINGwhile being stirred
4. 4
   درجة الحرارةThen the reaction mixture was cooled to room temperature
5. 5
   workup.DISTILLATIONwas then distilled under a reduced pressure
6. 6
   أخرىto remove all volatile materials
7. 7
   workup.ADDITIONMethanol was added to the concentrate
8. 8
   ترشيحthe thus-deposited solid was collected by filtration
9. 9
   أخرىThe obtained crude product
10. 10
    أخرىwas purified by silica gel chromatography
11. 11
    workup.ADDITIONmixed solvent as an eluent

الإجراء التجريبي

In a stream of argon, 0.53 g (2.14 mmol) of 1-pyreneboronic acid, 1.00 g (2.14 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 24.7 mg (0.0214 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 80 mL of toluene and 10 mL of ethanol, and the resultant suspension was heated to 60° C. To the suspension, 8.56 mL (8.56 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. Then the mixture was cooled to room temperature, and 0.64 g (3.21 mmol) of 4-(2-pyridyl)phenylboronic acid wad added. Then the mixture was heated to 70° C. and maintained at that temperature for 3 hours while being stirred. Then the reaction mixture was cooled to room temperature, and was 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 obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 0.37 g of the target 4,6-diphenyl-2-[5-(1-pyrenyl)-4′-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 26%).

المصدر