Toluene → 2-[4-(9-Anthryl)phenyl]benzoxazole

HRID 535240Notes

Reaction equation

HRID 535240 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.Br[C:20]1[C:21]2[C:26]([CH:27]=[C:28]3[C:33]=1[CH:32]=[CH:31][CH:30]=[CH:29]3)=[CH:25][CH:24]=[CH:23][CH:22]=2.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>[CH:22]1[C:21]2[C:26](=[CH:27][C:28]3[C:33]([C:20]=2[C:13]2[CH:14]=[CH:15][C:10]([C:2]4[O:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)=[CH:11][CH:12]=2)=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 740629-BromoanthraceneHCID 57958561(4-(Benzo[d]oxazol-2-yl)phenyl)boronic acid

Product 1

HCID 579673632-[4-(9-Anthryl)phenyl]benzoxazole

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In a 200 mL three-neck flask, 3.7 g (15 mmol) of 4-(benzoxazol-2-yl)phenylboronic acid, 3.9 g (15 mmol) of 9-bromoanthracene, 3.3 g (31 mmol) of sodium carbonate, 60 mL of toluene, 15 mL of ethanol, and 15 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, 0.16 g (0.14 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was stirred under nitrogen stream at 110° C. for 6 hours. After a certain period, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extracted solution and the organic layer were combined and washed with saturated saline, and the organic layer was dried with magnesium sulfate. The obtained 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 the filtrate was condensed. The solid was recrystallized with ethyl acetate/hexane, so that 3.3 g of target yellow powder was obtained in a yield of 57%.

Workup

  1. customThe mixture was degassed
  2. stirringthe mixture was stirred under nitrogen stream at 110° C. for 6 hours
  3. waitAfter a certain period
  4. extractionan aqueous layer was extracted with toluene
  5. extractionThe obtained extracted solution
  6. washwashed with saturated saline
  7. dry with materialthe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. customcondensed
  10. customto give a solid
  11. filtrationA toluene solution of the solid was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855)
  12. customcondensed
  13. customThe solid was recrystallized with ethyl acetate/hexane, so that 3.3 g of target yellow powder
  14. customwas obtained in a yield of 57%

Sources & evidence

ORD record
ord-dd7d3a32d5ec41138ba63877b4ab3f19
Source dataset
uspto-grants-2014_10
Patent number
US08859108B2

Reaction notes

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