1,4-Dibromobenzene → 4-Bromo-4'-methoxybiphenyl

HRID 1059133Notes

Reaction equation

HRID 1059133 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 78041,4-DibromobenzeneHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 40340054-Bromo-4'-methoxybiphenylYield 59.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Under an argon atmosphere, p-dibromobenzene (9.99 g), 4-methoxyphenylboronic acid (2.03 g) and tetrakistriphenylphosphine palladium (497 mg) were dissolved in dimethoxyethane (20 ml). A 2M aqueous sodium carbonate solution (20 ml) was added and the mixture was heated under reflux for 14 h. The reaction mixture was cooled to room temperature and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in ethyl acetate and insoluble materials were filtered off. The solvent was evaporated and the obtained solid was washed with hexane to give the title compound (2.09 g) as a colorless solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 h
  3. filtrationthe precipitated crystals were collected by filtration
  4. dissolutionThe obtained crystals were dissolved in ethyl acetate
  5. filtrationinsoluble materials were filtered off
  6. customThe solvent was evaporated
  7. washthe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-71bff236439e4efa92c838a15ed77bee
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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