Sodium Carbonate → HCID 67300876, compound

HRID 1014904Notes

Reaction equation

HRID 1014904 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=2)[CH:3]=1.[C:13]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>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>[C:13]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:18]=[CH:17][CH:16]=[C:15]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=3)[CH:3]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6405912,6-DibromonaphthaleneHCID 2734315(3-Phenylphenyl)boronic acid

Product 1

HCID 67300876HCID 67300876, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Commercial 2,6-dibromonaphthalene in an amount of 12 g, 11 g of commercial 3-biphenylboronic acid and 180 ml of toluene were mixed together. Then, 5.7 g of tetrakis(triphenylphosphine)palladium and 90 ml of a 2 M aqueous solution of sodium carbonate were added, and the reaction system was purged with argon. After the reaction mixture was heated under the refluxing condition for 7.5 hours, the reaction mixture was cooled by leaving standing. The formed crystals were separated by filtration and subjected to extraction with toluene. The obtained organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate, and the solvent was removed using an evaporator. The obtained residue was purified in accordance with the silica gel column chromatography (the developing solvent: hexane/toluene=5/1), and 7.8 g of 2-(biphenyl-3-yl)-6-bromonaphthalene was obtained as a white solid substance (the yield: 51%). 2-(Biphenyl-3-yl)-6-bromonaphthalene obtained above in an amount of 5.2 g, 6.4 g of 3-(9-phenylanthracen-10-yl)phenylboronic acid obtained in accordance with a conventional process, 60 ml of DME and 20 ml of toluene were mixed together. To the obtained solution, 0.67 g of tetrakis(triphenylphosphine)palladium and 60 ml of a 2 M aqueous solution of sodium carbonate were added, and the reaction system was purged with argon. After the reaction mixture was heated under the refluxing condition for 10 hours, the reaction mixture was cooled by leaving standing. The formed crystals were separated by filtration, washed with water and methanol and then with heated toluene, and 7.0 g of the object compound (AN-14) was obtained as a white solid substance (the yield: 74%). The obtained compound was examined in accordance with FD-MS (the field desorption mass analysis). Since it was found that m/z=658, which corresponded to C52H34=658, the obtained compound was identified to be AN-14.

Workup

  1. customthe reaction system was purged with argon
  2. temperatureAfter the reaction mixture was heated under the refluxing condition for 7.5 hours
  3. temperaturethe reaction mixture was cooled
  4. customby leaving standing
  5. customThe formed crystals were separated by filtration
  6. extractionsubjected to extraction with toluene
  7. washThe obtained organic layer was washed with water
  8. dry with materiala saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate
  9. customthe solvent was removed
  10. customan evaporator
  11. customThe obtained residue was purified in accordance with the silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-31464d3ede034fc8b87c2490c7d4f967
Source dataset
uspto-grants-2011_07
Patent number
US07985491B2

Reaction notes

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