Potassium Carbonate → 2-(7-Bromo-9,9-dimethylfluoren-2-yl)dibenzofuran

HRID 924545Notes

Reaction equation

HRID 924545 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.[CH:18]1[C:26]2[C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[O:23][C:22]=2[CH:21]=[CH:20][C:19]=1B(O)O.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:28]4[CH:29]=[CH:30][C:24]5[O:23][C:22]6[CH:21]=[CH:20][CH:19]=[CH:18][C:26]=6[C:25]=5[CH:27]=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 12032376Dibenzo(b,d)furan-2-ylboronic Acid (contains varying amounts of Anhydride)HCID 121238762,7-Dibromo-9,9-dimethylfluorene

Product 1

HCID 598664642-(7-Bromo-9,9-dimethylfluoren-2-yl)dibenzofuranYield 48%

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), dibenzo[b,d]furan-2-ylboronic acid (1.50 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 (8:1). 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: 48%).

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-753e050ac221420586fa1138811bb106
Source dataset
uspto-grants-2016_03
Patent number
US09281482B2

Reaction notes

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