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Potassium Carbonate → 2-[4-(10-Phenyl-9-anthryl)phenyl]benzoxazole

HRID 535236
Notes
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Reaction equation

HRID 535236 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.COCCOC>[C:16]1([C:9]2[C:8]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:2]([C:34]3[CH:35]=[CH:36][C:31]([C:23]4[O:22][C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[N:24]=4)=[CH:32][CH:33]=3)=[C:15]3[C:10]=2[CH:11]=[CH:12][CH:13]=[CH:14]3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 41558369-Bromo-10-phenyl-anthraceneHCID 57958561(4-(Benzo[d]oxazol-2-yl)phenyl)boronic acid

Product 1

HCID 579673212-[4-(10-Phenyl-9-anthryl)phenyl]benzoxazoleYield 81.9%

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

In a 50 mL three-neck flask, 1.0 g (3.0 mmol) of 9-bromo-10-phenylanthracene, 0.72 g (3.0 mmol) of 4-(benzoxazol-2-yl)phenylboronic acid, 0.10 g (0.32 mmol) of tri(ortho-tolyl)phosphine, 20 mL of ethylene glycol dimethyl ether (DME), and 3.0 mL (6.0 mmol) of a 2.0 M potassium carbonate solution 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, 14 mg (0.062 mmol) of palladium(II) acetate was added, and the mixture was stirred under nitrogen stream at 80° 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 mixture was gravity filtered, and the obtained filtrate was condensed to give an oily substance. The oily substance was purified by silica gel column chromatography (toluene:hexane=2:1) and recrystallized with toluene/methanol, giving 1.1 g of the target pale yellow powder in a yield of 81%.

Workup

  1. customThe mixture was degassed
  2. stirringthe mixture was stirred under nitrogen stream at 80° 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 an oily substance
  11. customThe oily substance was purified by silica gel column chromatography (toluene:hexane=2:1)
  12. customrecrystallized with toluene/methanol

Sources & evidence

ORD record
ord-bbc884e4a01f4227a18865eb1ab7b307
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859108B2

Reaction notes

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