Ethanol → (Biphenyl-4-yl)-[4-(9,9-dimethyl-7,10-diphenylacridan-2-yl)phenyl]-phenylamine

HRID 532317Notes

Reaction equation

HRID 532317 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: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.CO>[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:13]2[CH:4]=[CH:3][C:2]([C:2]3[CH:15]=[CH:14][C:13]4[N:12]([C:11]5[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:16]5[C:17](=[CH:18][C:19]([C:16]6[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=6)=[CH:20][CH:21]=5)[C:5]([CH3:28])([CH3:29])[C:4]=4[CH:3]=3)=[CH:15][CH:14]=2)[C:11]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[CH:41][CH:40]=1

Participants

7

Reactant 4

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

Product 1

HCID 89454940(Biphenyl-4-yl)-[4-(9,9-dimethyl-7,10-diphenylacridan-2-yl)phenyl]-phenylamineYield 68%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
72 °C

Procedure

2-Bromo-9,9-dimethyl-7,10-diphenylacridan (3.2 g), (biphenyl-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaboran-2-yl)phenyl]-phenylamine (3.6 g), toluene (40 ml), ethanol (10 ml), and a 2M potassium carbonate aqueous solution (11 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 (0.26 g) and stirred at 72° C. for 7 hours. The mixture was allowed to cool to a room temperature, and methanol (50 ml) was added. A precipitated solid was collected by filtration and washed with water to obtain a red brown crude product. The crude product was dissolved by adding toluene (100 ml) and subjected to adsorptive purification twice using silica gel (3.7 g). The product was then crystallized with toluene/methanol to obtain a white powder of (biphenyl-4-yl)-[4-(9,9-dimethyl-7,10-diphenylacridan-2-yl)phenyl]-phenylamine (3.42 g; yield 68%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto cool to a room temperature
  3. filtrationA precipitated solid was collected by filtration
  4. washwashed with water
  5. customto obtain a red brown crude product
  6. custompurification twice using silica gel (3.7 g)
  7. customThe product was then crystallized with toluene/methanol

Sources & evidence

ORD record
ord-5e93a344a57d46a39e9db57ac922277e
Source dataset
uspto-grants-2014_10
Patent number
US08852759B2

Reaction notes

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