Sodium Carbonate → HCID 15506413, compound

HRID 1515574Notes

Reaction equation

HRID 1515574 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O)=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:17]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 113099-BromophenanthreneHCID 2921892-Formylphenylboronic acid

Product 1

HCID 15506413HCID 15506413, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Under an argon atmosphere, 25.7 g of 9-bromophenanthrene, 16.5 g of 2-formylphenylboronic acid and 2.31 g of tetraxis(triphenylphosphine)palladium(0) were placed in a flask. 340 mL of dimethoxyethane (DME) and 170 mL of a 2M aqueous sodium carbonate solution were added to this flask, and the resultant was refluxed with stirring while heating for 8 hours. After cooling to room temperature, an aqueous phase was removed. An organic phase was washed with water and saturated brine, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The residue was purified by means of silica gel column chromatography, whereby 25.0 g (yield: 89%) of intended 9-(2-formylphenyl)phenanthrene was obtained.

Workup

  1. temperaturethe resultant was refluxed
  2. temperaturewhile heating for 8 hours
  3. customan aqueous phase was removed
  4. washAn organic phase was washed with water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationAfter the magnesium sulfate was filtered out
  7. concentrationthe organic phase was concentrated
  8. customThe residue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-d7bf684ef02e41a39ec0a6693e89be4a
Source dataset
uspto-grants-2012_07
Patent number
US08222637B2

Reaction notes

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