Sodium Carbonate → HCID 57264076, compound

HRID 539254

Reaction equation

HRID 539254 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1Br.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH3:10])[C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 612591-Bromo-2-fluorobenzeneHCID 51564912,3-Dimethoxybenzeneboronic acid

Product 1

HCID 57264076HCID 57264076, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In the atmosphere of argon, 18.2 g of 2,3-dimethoxyphenylboronic acid, 17.5 g of 2-fluorobromobenzene, 2.31 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane and 150 mL of an aqueous 2M sodium carbonate solution were placed in a flask. The resulting mixture was stirred with heating under reflux for 8 hours. After cooling to room temperature, an aqueous phase was removed, and an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate and then concentrated. Residues were purified by silica gel column chromatography, whereby 19.7 g of (yield 85%) of 2′-fluoro-2,3-dimethoxybiphenyl was obtained.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hours
  3. customan aqueous phase was removed
  4. washan organic phase was washed with saturated saline
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. concentrationconcentrated
  7. customResidues were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-61096a40444346a482859d4c2af2deb3
Source dataset
uspto-grants-2014_10
Patent number
US08866135B2

Linked notes

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