Ethanol → HCID 68102860, compound

HRID 532319Notes

Reaction equation

HRID 532319 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[N:12]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:18][CH:17]=3)[C:11]3[C:6](=[CH:7][C:8]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:9][CH:10]=3)[C:5]([CH3:35])([CH3:34])[C:4]=2[CH:3]=1.[CH2:36](O)[CH3:37].C(=O)([O-])[O-].[K+].[K+]>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.C1(C)C=CC=CC=1.CO>[C:8]1([C:37]2[CH:36]=[CH:33][CH:28]=[CH:29][CH:30]=2)[CH:9]=[CH:10][C:11]([N:12]([C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][CH:21]=2)[C:25]2[CH:24]=[CH:23][C:22]([C:19]3[CH:20]=[CH:21][C:16]4[N:12]([C:11]5[CH:10]=[CH:9][C:8]([C:28]6[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=6)=[CH:7][CH:6]=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]([CH3:34])([CH3:35])[C:17]=4[CH:18]=3)=[CH:27][CH:26]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 89455051HCID 89455051, compound

Product 1

HCID 68102860HCID 68102860, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
72 °C

Procedure

2-Bromo-10-(biphenyl-4-yl)-9,9-dimethyl-7-phenylacridan (2.5 g), bis(biphenyl-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaboran-2-yl)phenyl]amine (3.0 g), toluene (37 ml), ethanol (9.3 ml), and a 2M potassium carbonate aqueous solution (7.2 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 (0.11 g) and stirred at 72° C. for 8.5 hours. The mixture was allowed to cool to a room temperature, and methanol (40 ml) was added. A precipitated solid was collected by filtration and washed with water to obtain an orange crude product. The crude product was dissolved by adding toluene (360 ml), purified by adsorption using silica gel (3.6 g), and crystallized with toluene/methanol three times. Further, methanol (60 ml) was added to the product, and the product was washed and purified by heating under reflux to obtain a white powder of bis(biphenyl-4-yl)-[4-{10-(biphenyl-4-yl)-9,9-dimethyl-7-phenylacridan-2-yl}phenyl]amine (3.04 g; yield 75%).

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 an orange crude product
  6. custompurified by adsorption
  7. customcrystallized with toluene/methanol three times
  8. additionFurther, methanol (60 ml) was added to the product
  9. washthe product was washed
  10. custompurified
  11. temperatureby heating
  12. temperatureunder reflux

Sources & evidence

ORD record
ord-64e821bf92634b25965af4931a7555bf
Source dataset
uspto-grants-2014_10
Patent number
US08852759B2

Reaction notes

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