Sodium Hydroxide → HCID 86669961, compound

HRID 2273505Notes

Reaction equation

HRID 2273505 reaction equation
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:19]1[CH:20]=[C:21]([C:26]2[N:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:29]=[C:28]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:27]=2)[CH:22]=[C:23](Br)[CH:24]=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>[CH:1]1[C:14]2[CH:13]=[C:12]([C:19]3[CH:20]=[C:21]([C:26]4[N:31]=[C:30]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[N:29]=[C:28]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[N:27]=4)[CH:22]=[C:23]([C:13]4[C:14]5[C:5]([C:6]6[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=6[CH:12]=4)=[CH:4][CH:3]=[CH:2][CH:1]=5)[CH:24]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 117757049-Phenanthracenylboronic acidHCID 583826152-(3,5-Dibromophenyl)-4,6-diphenyl-1,3,5-triazine

Product 1

HCID 86669961HCID 86669961, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of argon, 1.37 g (6.16 mmol) of 9-phenanthreneboronic acid, 1.20 g (2.57 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 72.1 mg (0.103 mmol) of dichlorobis(triphenylphosphine)palladium were suspended in 75 mL of tetrahydrofuran, and the temperature of the obtained suspension was elevated to 70° C. 4.81 mL (19.3 mmol) of an aqueous 4N NaOH solution was gradually added dropwise to the suspension, and the obtained mixture was distilled under reflux for 5 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 1.13 g of the target 2-[3,5-di(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine as grayish white solid (yield: 66%).

Workup

  1. customwas elevated to 70° C
  2. distillationthe obtained mixture was distilled
  3. temperatureunder reflux for 5 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-dd257d75ae044bd9a28b480cdeea242d
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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