9-Bromoanthracene → 4-(Anthracen-9-yl)benzaldehyde

HRID 901763Notes

Reaction equation

HRID 901763 reaction equation
Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17].[F-].[K+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C1(C)C=CC=CC=1.O>[CH:16]([C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:3]3[C:8]([CH:9]=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:20][CH:19]=1)=[O:17]

Participants

9

Reactant 3

HCID 740629-BromoanthraceneHCID 522689Potassium FluorideHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 221380334-(Anthracen-9-yl)benzaldehydeYield 78%

Reagents, catalysts & solvents 5

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of argon, 9-bromoanthracene (3.9 g, 15 mmole), 4-formylphenylboronic acid (2.5 g, 17 mmole, 1.1 eq), potassium fluoride (3.2 g, 56 mmole, 3 eq) and tris(dibenzylideneacetone)-dipalladium(0) (0.07 g, 76 mmole, 1% Pd) were suspended in anhydrous THF (25 ml). To the obtained suspension, a toluene solution of tri-t-butylphosphine (66%, 0.06 ml, 0.2 mmole, 1.3 eq to Pd) was added and the resultant mixture was heated under refluxing for 10 hours. To the reaction mixture, water (50 ml) and toluene (150 ml) were added. The formed organic layer was separated, washed with a saturated aqueous solution of sodium chloride (50 ml) and dried with magnesium sulfate. Then, the solvent was removed by distillation and a light yellow solid was obtained. The obtained solid was purified by the column chromatography (silica gel/ hexane+50% dichloromethane) and a light yellow solid (3.3 g, 78%) were obtained.

Workup

  1. temperatureunder refluxing for 10 hours
  2. customThe formed organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride (50 ml)
  4. dry with materialdried with magnesium sulfate
  5. customThen, the solvent was removed by distillation
  6. customa light yellow solid was obtained
  7. customThe obtained solid was purified by the column chromatography (silica gel/ hexane+50% dichloromethane)

Sources & evidence

ORD record
ord-af2de6e6713d4ec8ba202ee54df058c2
Source dataset
uspto-grants-2008_04
Patent number
US07361796B2

Reaction notes

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