Sodium Hydroxide → HCID 86669962, compound

HRID 2273511Notes

Reaction equation

HRID 2273511 reaction equation
Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:16]1([C:22]2[N:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:25]=[CH:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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:14]1[C:15]2[C:10](=[CH:9][C:8]3[C:3]([C:2]=2[C:18]2[CH:17]=[C:16]([C:22]4[N:23]=[C:24]([C:2]5[CH:3]=[CH:8][CH:9]=[CH:10][CH:15]=5)[N:25]=[C:26]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:27]=4)[CH:21]=[C:20]([C:2]4[C:15]5[C:10]([CH:9]=[C:8]6[C:3]=4[CH:4]=[CH:5][CH:6]=[CH:7]6)=[CH:11][CH:12]=[CH:13][CH:14]=5)[CH:19]=2)=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 159122,4-diphenyl-1,3,5-triazineHCID 740629-Bromoanthracene

Product 1

HCID 86669962HCID 86669962, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of argon, 0.62 g (2.13 mmol) of 9-bromoanthracene, 0.50 g (0.89 mmol) of 2-(3,5-bis(4,4,5,5-tetramethyl)-1,3,2-dioxabororan-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine and 18.7 mg (0.027 mmol) of dichlorobis-(triphenylphosphine)palladium were suspended in 40 mL of tetrahydrofuran, and the temperature of the obtained suspension was elevated to 70° C. 1.34 mL (5.34 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 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 purified by silica gel column chromatography using a hexane/chloroform (5:1-2:1) mixed solvent as an eluent to give 0.32 g of the target 2-[3,5-di(9-anthryl)phenyl]-4,6-diphenyl-1,3,5-triazine as white solid (yield: 54%).

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. 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. customwas purified by silica gel column chromatography
  11. additionmixed solvent as an eluent

Sources & evidence

ORD record
ord-829d75a91fd54280a105d5df14065040
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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