Sodium Carbonate → HCID 67775933, compound

HRID 470731Notes

Reaction equation

HRID 470731 reaction equation
[CH3:1][O:2][C:3]1[C:4](B(O)O)=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1Br.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:1][O:2][C:3]1[C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[F:16])=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 612591-Bromo-2-fluorobenzeneHCID 108889523-Methoxynaphthalene-2-boronic acid

Product 1

HCID 67775933HCID 67775933, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In the atmosphere of argon, 14.3 g of 3-methoxynaphthalene-2-boronic acid, 12.4 g of 2-fluorobromobenzene, 1.64 g of tetrakistriphenylphosphine palladium (0), 220 mL of 1,2-dimethoxyethane, 110 mL of a 2M aqueous solution of sodium carbonate were placed in a flask, and the resulting mixture was stirred with heating under reflux for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed, and then 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 13.4 g (yield: 75%) of 2-methoxy-3-(2-fluorophenyl)naphthalene was obtained.

Workup

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

Sources & evidence

ORD record
ord-1bcd32c6139640edbd21e47057f42748
Source dataset
uspto-grants-2014_01
Patent number
US08629430B2

Reaction notes

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