Sodium Carbonate → HCID 15506413, compound

HRID 2274126Notes

Reaction equation

HRID 2274126 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+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[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

6

Reactant 3

HCID 10340Sodium CarbonateHCID 113099-BromophenanthreneHCID 2921892-Formylphenylboronic acid

Product 1

HCID 15506413HCID 15506413, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under the atmosphere of argon, 25.7 g of 9-bromophenathrene, 16.5 g of 2-formylphenylboronic acid and 2.31 g of tetrakis(triphenylphosphine)palladium (0) were placed in a flask. To the resulting mixture, 340 mL of DME and 170 mL of an aqueous 2M sodium carbonate solution were added, followed by stirring under reflux while heating for 8 hours. After cooling to room temperature, an aqueous phase was removed. An organic phase was washed with water and saturated saline, and dried with magnesium sulfate. After filtering off magnesium sulfate, the organic phase was concentrated. The residues were purified by silica gel column chromatography, whereby 25.0 g (yield 89%) of 9-(2-formylphenyl)phenanthrene as an intended product was obtained.

Workup

  1. temperatureunder reflux
  2. temperaturewhile heating for 8 hours
  3. customan aqueous phase was removed
  4. washAn organic phase was washed with water and saturated saline
  5. dry with materialdried with magnesium sulfate
  6. filtrationAfter filtering off magnesium sulfate
  7. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-506cefb1340944bbaae4aa70ce1c0ed5
Source dataset
uspto-grants-2015_09
Patent number
US09126943B2

Reaction notes

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