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Toluene → 2-[3-Chloro-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine

HRID 2273509
Notes
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Reaction equation

HRID 2273509 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]([Cl:25])[CH:24]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[Cl:25][C:23]1[CH:22]=[C:21]([C:26]2[N:27]=[C:28]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:29]=[C:30]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:31]=2)[CH:20]=[C:19]([C:12]2[C:11]3[C:6]([C:5]4[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=4[CH:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 117757049-Phenanthracenylboronic acidHCID 441387662-(3-Bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine

Product 1

HCID 866699662-[3-Chloro-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazineYield 91%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

In a stream of argon, 0.52 g (2.36 mmol) of 9-phenanthreneboronic acid, 0.91 g (2.15 mmol) of 2-(3-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine and 24.8 mg (0.022 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent comprised of 80 mL of toluene and 10 mL of ethanol, and the temperature of the obtained suspension was elevated to 60° C. 6.45 mL (6.45 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise to the suspension, and the obtained mixture was distilled under reflux for 18 hours. The resultant reaction mixture was cooled 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 dissolved in chloroform and the obtained solution was filtered by celite. The filtrate was distilled to remove all volatile materials to give 1.02 g of an intermediate 2-[3-chloro-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine as grayish white solid (yield: 91%).

Workup

  1. customwas elevated to 60° C
  2. distillationthe obtained mixture was distilled
  3. temperatureunder reflux for 18 hours
  4. customThe resultant reaction mixture
  5. distillationdistilled under a reduced pressure
  6. customto remove all volatile materials
  7. additionMethanol was added to the concentrate
  8. filtrationthe thus-deposited solid was collected by filtration
  9. customThe thus-obtained crude product
  10. filtrationthe obtained solution was filtered by celite
  11. distillationThe filtrate was distilled
  12. customto remove all volatile materials

Sources & evidence

ORD record
ord-710a18d22a634d6ebd1945c9c3c447af
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09120773B2

Reaction notes

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