Toluene → 2-{4-[10-(Biphenyl-4-yl)-9-anthryl]phenyl}benzoxazole

HRID 535243Notes

Reaction equation

HRID 535243 reaction equation
Br[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[O:23][C:24]4[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=4[N:26]=3)=[CH:18][CH:17]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[C:31]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=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.O.C(O)C>[C:31]1([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:36]=[CH:35][C:34]([C:2]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:23][C:24]5[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=5[N:26]=4)=[CH:18][CH:17]=3)=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[CH:7]3)=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 57967305HCID 57967305, compound

Product 1

HCID 579673342-{4-[10-(Biphenyl-4-yl)-9-anthryl]phenyl}benzoxazoleYield 49.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a 100 mL three-neck flask, 0.91 g (2.0 mmol) of 2-[4-(10-bromo-9-anthryl)phenyl]benzoxazole, 0.44 g (2.2 mmol) of 4-biphenylboronic acid, 0.47 g (4.4 mmol) of sodium carbonate, 10 mL of toluene, 3 mL of ethanol, and 3 mL of water were placed. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 29 mg (0.025 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was stirred under nitrogen stream at 80° C. for 13 hours. After a certain period, the mixture was cooled to room temperature, and the precipitated solid was obtained by suction filtration and washed with water. A toluene solution of the obtained solid was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) and alumina, and the filtrate was condensed to give a solid. The solid was recrystallized with toluene/hexane, giving 0.52 g of the target white powder. Further, an aqueous layer of the filtrate which was obtained through suction filtration after stirring was extracted with toluene. The obtained extracted solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was gravity filtered, and the filtrate was condensed to give a solid. A toluene solution of the solid was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) and alumina, and the filtrate was condensed to give a solid. The solid was recrystallized with toluene/hexane, giving 0.47 g of the target white powder. In this manner, a total of 0.99 g of the target white solid was obtained in a yield of 93%.

Workup

  1. customThe mixture was degassed
  2. stirringthe mixture was stirred under nitrogen stream at 80° C. for 13 hours
  3. waitAfter a certain period
  4. customthe precipitated solid was obtained by suction filtration
  5. washwashed with water
  6. filtrationA toluene solution of the obtained solid was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) and alumina
  7. customcondensed
  8. customto give a solid
  9. customThe solid was recrystallized with toluene/hexane

Sources & evidence

ORD record
ord-4f8e3ffd3f2f48b3b1e00a160446b022
Source dataset
uspto-grants-2014_10
Patent number
US08859108B2

Reaction notes

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