Sodium Carbonate → 3-bromo-m-terphenyl

HRID 1014908Notes

Reaction equation

HRID 1014908 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.[C:9]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:19]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 2734315(3-Phenylphenyl)boronic acid

Product 1

HCID 215369133-bromo-m-terphenylYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Commercial 3-bromoiodobenzene in an amount of 11 g, 8.7 g of commercial 3-biphenylboronic acid and 130 ml of toluene were mixed together. To the resultant mixture, 0.9 g of tetrakis(triphenyl-phosphine)palladium and 75 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 8 hours, the reaction mixture was cooled by leaving standing. The formed crystals were separated by filtration and subjected to extraction with toluene. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate. The solvent was removed using an evaporator. The residue was purified in accordance with the silica gel column chromatography (the developing solvent: hexane), and 11.8 g of 3-bromo-m-terphenyl was obtained as a white solid substance (the yield: 96%).

Workup

  1. customthe reaction system was purged with argon
  2. temperatureAfter the reaction mixture was heated under the refluxing condition for 8 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 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 residue was purified in accordance with the silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-1fb825d0b0034f1f8394fa68c47bc624
Source dataset
uspto-grants-2011_07
Patent number
US07985491B2

Reaction notes

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