Potassium Carbonate → Fluorene

HRID 720226Notes

Reaction equation

HRID 720226 reaction equation
C([SiH2]C1C=CC=CC=1)CCC.C([C:20]1(CCCCCCCC)[C:32]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)CCCCCCC.[B].BrC1C=CC2C3C(=CC(Br)=CC=3)C(CCCCCCCC)(CCCCCCCC)C=2C=1.C(=O)([O-])[O-].[K+].[K+]>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.C1(C)C=CC=CC=1.O.C1COCC1>[CH:22]1[C:21]2[CH2:20][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 52153212,7-Dibromo-9,9-di-n-octylfluoreneHCID 5462311BoronHCID 162138639,9-Dioctyl-9H-fluoreneHCID 102466365Butylphenylsilane2×

Product 1

HCID 6853Fluorene

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Under a nitrogen gas atmosphere, 289 mg (0.235 mmol) of butylphenylsilane (compound 14), 750 mg (1.17 mmol) of 9,9-dioctylfluorene with boron structures introduced onto the 2 and 7 positions, 515 mg (0.935 mmol) of 2,7-dibromo-9,9-dioctylfluorene, 2.22 g (16.1 mmol) of potassium carbonate, 15 ml of THF and 8 ml of distilled water were added to a 100 ml three-necked flask equipped with a reflux condenser, and this mixture was heated to 60° C. After the dissolution of the substrate was confirmed, one full spatula of tetrakis(triphenylphosphine)palladium was added, and the mixture was heated and agitated for approximately 48 hours. When toluene was added following cooling and the solvent was distilled away as far as possible, a high-viscosity substance was obtained.

Workup

  1. additionwere added to a 100 ml three-necked flask
  2. customequipped with a reflux condenser
  3. dissolutionAfter the dissolution of the substrate
  4. temperaturethe mixture was heated
  5. temperaturefollowing cooling
  6. distillationthe solvent was distilled away as far as possible, a high-viscosity substance
  7. customwas obtained

Sources & evidence

ORD record
ord-260e3a72b2ae429187c42cf0bdb4e5f1
Source dataset
uspto-grants-2006_11
Patent number
US07135242B2

Reaction notes

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