Toluene → 2-{4-[10-(1-Naphthyl)-9-anthryl]phenyl}benzoxazole

HRID 535242Notes

Reaction equation

HRID 535242 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(B(O)O)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[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:2]2[C:3]3[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:9]([C:16]3[CH:17]=[CH:18][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:20][CH:21]=3)=[C:10]3[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]3)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 57967305HCID 57967305, compound

Product 1

HCID 579673692-{4-[10-(1-Naphthyl)-9-anthryl]phenyl}benzoxazoleYield 78.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In a 50 mL three-neck flask, 0.90 g (2.0 mmol) of 2-[4-(10-bromo-9-anthryl)phenyl]benzoxazole, 0.37 g (2.2 mmol) of 1-naphthaleneboronic acid, 0.50 g (4.7 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, 32 mg (0.027 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was stirred under nitrogen stream at 80° C. for 7 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 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 obtained filtrate was condensed to give a solid. The solid was purified by silica gel column chromatograghy (toluene:hexane=2:1) and recrystallized with toluene/hexane, giving 0.78 g of the target pale yellow powder in a yield of 78%.

Workup

  1. customThe mixture was degassed
  2. stirringthe mixture was stirred under nitrogen stream at 80° C. for 7 hours
  3. waitAfter a certain period
  4. extractionan aqueous layer was extracted with toluene
  5. extractionThe obtained extracted solution
  6. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline
  7. dry with materialthe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. customcondensed
  10. customto give a solid
  11. customThe solid was purified by silica gel column chromatograghy (toluene:hexane=2:1)
  12. customrecrystallized with toluene/hexane

Sources & evidence

ORD record
ord-2766f3b3e8bf4841ac36c467a6cc47c6
Source dataset
uspto-grants-2014_10
Patent number
US08859108B2

Reaction notes

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