Sodium Hydroxide → HCID 86669963, compound

HRID 2273506Notes

Reaction equation

HRID 2273506 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][CH:37]=[CH:36][CH:35]=3)[N:31]=[C:30]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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][CH:37]=[CH:36][CH:35]=4)[N:31]=[C:30]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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 acidHCID 583826152-(3,5-Dibromophenyl)-4,6-diphenyl-1,3,5-triazine

Product 1

HCID 86669963HCID 86669963, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-a4e8bd05e1fe45a59dc8805367dead79
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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