Potassium Carbonate → HCID 118112465, compound

HRID 924546Notes

Reaction equation

HRID 924546 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH3:17])([CH3:16])[C:4]=2[CH:3]=1.[C:18]1([N:24]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:25]2[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[Br:15][C:8]1[CH:7]=[C:6]2[C:11]([C:12]3[CH:13]=[CH:14][C:2]([C:29]4[CH:30]=[C:25]([CH:26]=[CH:27][CH:28]=4)[N:24]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:3][C:4]=3[C:5]2([CH3:16])[CH3:17])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 121238762,7-Dibromo-9,9-dimethylfluoreneHCID 90028501HCID 90028501, compound

Product 1

HCID 118112465HCID 118112465, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 22272177Toluene waterSolvent

Procedure

2,7-dibromo-9,9-dimethyl-9H-fluorene (5.0 g, 14.201 mmol), 3-(diphenylamino)phenylboronic acid (2.05 g, 7.10 mmol), Pd(pph3)4 (820 mg, 0.71 mmol), K2CO3 (1.96 g, 14.201 mmol) were put in a 250 mL two-neck flask and dissolved in toluene/H2O. The solution was refluxed and stirred for 12 hours. After completion of the reaction, the solution was distilled under reduced pressure to remove the solvent. The resultant was columned with a solution of hexane and methylenechloride (4:1). The solution was distilled under reduced pressure and was re-crystallized in a solution of methylene chloride and petroleum ether such that the white solid compound was obtained, (1.50 g, yield: 41%).

Workup

  1. temperatureThe solution was refluxed
  2. customAfter completion of the reaction
  3. distillationthe solution was distilled under reduced pressure
  4. customto remove the solvent
  5. distillationThe solution was distilled under reduced pressure
  6. customwas re-crystallized in a solution of methylene chloride and petroleum ether such that the white solid compound
  7. customwas obtained

Sources & evidence

ORD record
ord-b33368b90eea475e86d448fee4bb9c2c
Source dataset
uspto-grants-2016_03
Patent number
US09281482B2

Reaction notes

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