Ethanol → [4-(9,9-Dimethyl-7,10-diphenylacridan-2-yl)phenyl]-diphenylamine

HRID 532315Notes

Reaction equation

HRID 532315 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]3[C:6](=[CH:7][C:8](C4C=CC=CC=4)=[CH:9][CH:10]=3)C(C)(C)[C:4]=2[CH:3]=1.[C:30]1([N:36]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:37]2[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[C:52]1(C)[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.[C:59](=O)([O-])[O-].[K+].[K+].[CH2:65](O)[CH3:66]>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>[CH3:59][C:65]1([CH3:66])[C:38]2[CH:39]=[C:40]([C:19]3[CH:20]=[CH:21][C:16]([N:12]([C:13]4[CH:14]=[CH:15][CH:2]=[CH:3][CH:4]=4)[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:17][CH:18]=3)[CH:41]=[CH:42][C:37]=2[N:36]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:30]2[C:35]1=[CH:34][C:33]([C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)=[CH:32][CH:31]=2

Participants

7

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 11430Potassium CarbonateHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)HCID 709361152-Bromo-9,9-dimethyl-7,10-diphenylacridan

Product 1

HCID 68102861[4-(9,9-Dimethyl-7,10-diphenylacridan-2-yl)phenyl]-diphenylamineYield 54%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
68 °C

Procedure

2-Bromo-9,9-dimethyl-7,10-diphenylacridan (2.54 g), 4-(diphenylamino)phenylboronic acid (1.75 g), toluene (25 ml), ethanol (2 ml), and a 2M potassium carbonate aqueous solution (9 ml) were added to a reaction vessel in a nitrogen atmosphere and aerated with nitrogen gas for 30 min under ultrasonic irradiation. The mixture was heated after adding tetrakis(triphenylphosphine)palladium (0.20 g) and stirred at 68° C. for 8 hours. The mixture was allowed to cool to a room temperature, and an organic layer was collected by a liquid separating operation. The organic layer was dried with magnesium sulfate and concentrated under reduced pressure to obtain a yellow amorphous crude product. The crude product was recrystallized with n-hexane, dissolved by adding toluene (30 ml), and purified by adsorption using silica gel (1.17 g Methanol (20 ml) was added to this solution to precipitate crystals, and the crystals were further purified by recrystallization using toluene/methanol to obtain a white powder of [4-(9,9-dimethyl-7,10-diphenylacridan-2-yl)phenyl]-diphenylamine (1.9 g; yield 54%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto cool to a room temperature
  3. customan organic layer was collected by a liquid
  4. customseparating operation
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a yellow amorphous crude product
  8. customThe crude product was recrystallized with n-hexane
  9. dissolutiondissolved
  10. additionby adding toluene (30 ml)
  11. custompurified by adsorption
  12. additionwas added to this solution
  13. customto precipitate crystals
  14. customthe crystals were further purified by recrystallization

Sources & evidence

ORD record
ord-134612948603449f9579c4e7934490c0
Source dataset
uspto-grants-2014_10
Patent number
US08852759B2

Reaction notes

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