Sodium Hydroxide → 2-[3,5-Di(1-pyrenyl)phenyl]-4,6-di-p-tolyl-1,3,5-triazine

HRID 2273508Notes

Reaction equation

HRID 2273508 reaction equation
[C:1]1(B(O)O)[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.Br[C:21]1[CH:22]=[C:23]([C:28]2[N:33]=[C:32]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)[N:31]=[C:30]([C:41]3[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=3)[N:29]=2)[CH:24]=[C:25](Br)[CH:26]=1.[OH-].[Na+]>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]1([C:21]2[CH:22]=[C:23]([C:28]3[N:33]=[C:32]([C:34]4[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=4)[N:31]=[C:30]([C:41]4[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=4)[N:29]=3)[CH:24]=[C:25]([C:8]3[C:7]4[C:16]5=[C:15]6[C:4](=[CH:5][CH:6]=4)[CH:3]=[CH:2][CH:1]=[C:14]6[CH:13]=[CH:12][C:11]5=[CH:10][CH:9]=3)[CH:26]=2)[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5084102Pyren-1-ylboronic acid2×HCID 583826282-(3,5-Dibromophenyl)-4,6-di-p-tolyl-1,3,5-triazine

Product 1

HCID 866699652-[3,5-Di(1-pyrenyl)phenyl]-4,6-di-p-tolyl-1,3,5-triazineYield 51%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of argon, 1.20 g (4.87 mmol) of 1-pyreneboronic acid, 1.50 g (3.03 mmol) of 2-(3,5-dibromophenyl)-4,6-di-p-tolyl-1,3,5-triazine and 57 mg (0.081 mmol) of dichlorobis-(triphenylphosphine)palladium were suspended in 135 mL of tetrahydrofuran, and the temperature of the obtained suspension was elevated to 70° C. 3.81 mL (15.2 mmol) of an aqueous 4N NaOH solution was gradually added dropwise to the suspension, and the obtained mixture was distilled under reflux for 2 hours. Then, 29 mg (0.041 mmol) of dichlorobis(triphenylphosphine)palladium was added, followed by distillation under reflux for 2 hours. Further, 0.20 g (0.81 mmol) of 1-pyreneboronic acid was added, followed by distillation under reflux for 2 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. The recrystallization by o-xylene was repeated three times in total to give 1.14 g of the target 2-[3,5-di(1-pyrenyl)phenyl]-4,6-di-p-tolyl-1,3,5-triazine as grayish white solid (yield: 51%).

Workup

  1. customwas elevated to 70° C
  2. distillationthe obtained mixture was distilled
  3. temperatureunder reflux for 2 hours
  4. distillationfollowed by distillation
  5. temperatureunder reflux for 2 hours
  6. distillationfollowed by distillation
  7. temperatureunder reflux for 2 hours
  8. customThe resultant reaction mixture
  9. waitwas left
  10. customto stand to room temperature
  11. distillationdistilled under a reduced pressure
  12. customto remove all volatile materials
  13. additionMethanol was added to the concentrate
  14. filtrationthe thus-deposited solid was collected by filtration
  15. customThe thus-obtained crude product
  16. customwas recrystallized from o-xylene
  17. customThe recrystallization by o-xylene

Sources & evidence

ORD record
ord-52a00375269e4eba978cea9723c274b5
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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