Ethanol → Bis(biphenyl-4-yl)-[4-(9,9-dimethyl-7,10-diphenylacridan-2-yl)phenyl]amine

HRID 532318Notes

Reaction equation

HRID 532318 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]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:9][CH:10]=3)[C:5]([CH3:29])([CH3:28])[C:4]=2[CH:3]=1.[CH2:30](O)[CH3:31].C(=O)([O-])[O-].[K+].[K+].[C:39]1([CH3:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>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:39]1([C:45]2[CH:31]=[CH:30][CH:29]=[CH:5][CH:28]=2)[CH:44]=[CH:43][C:42]([N:12]([C:11]2[CH:10]=[CH:9][C:8]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:7][CH:6]=2)[C:25]2[CH:26]=[CH:27][C:22]([C:8]3[CH:9]=[CH:10][C:11]4[N:12]([C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:13]5[C:4](=[CH:3][C:2]([C:15]6[CH:2]=[CH:3][CH:4]=[CH:13][CH:14]=6)=[CH:15][CH:14]=5)[C:5]([CH3:29])([CH3:28])[C:6]=4[CH:7]=3)=[CH:23][CH:24]=2)=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1140Toluene2×HCID 11430Potassium CarbonateHCID 709361152-Bromo-9,9-dimethyl-7,10-diphenylacridan

Product 1

HCID 68102855Bis(biphenyl-4-yl)-[4-(9,9-dimethyl-7,10-diphenylacridan-2-yl)phenyl]amineYield 64%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
72 °C

Procedure

2-Bromo-9,9-dimethyl-7,10-diphenylacridan (2.9 g), bis(biphenyl-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaboran-2-yl)phenyl]amine (4.0 g), toluene (44 ml), ethanol (11 ml), and a 2M potassium carbonate aqueous solution (8.4 ml) were added to a nitrogen-substituted reaction vessel and aerated with nitrogen gas for 30 min under ultrasonic irradiation. The mixture was heated after adding tetrakis(triphenylphosphine)palladium (0.23 g) and stirred at 72° C. for 4.5 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 red crude product. The crude product was dissolved by adding toluene (75 ml), purified by adsorption using silica gel (5.2 g), and purified by recrystallization using toluene/methanol to obtain a whitish powder of bis(biphenyl-4-yl)-[4-(9,9-dimethyl-7,10-diphenylacridan-2-yl)phenyl]amine (3.19 g; yield 64%).

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 red crude product
  8. custompurified by adsorption
  9. custompurified by recrystallization

Sources & evidence

ORD record
ord-c6a797005651418cae387069c82cde7a
Source dataset
uspto-grants-2014_10
Patent number
US08852759B2

Reaction notes

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