Sodium Carbonate → HCID 15506413, compound

HRID 2405448Notes

Reaction equation

HRID 2405448 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.COC>[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 8254Dimethyl EtherSolvent

Procedure

A flask was charged with 25.7 g of 9-bromophenanthrene, 16.5 g of 2-formylphenylboronic acid, and 2.31 g of tetrakis(triphenylphosphine)palladium(0) in an argon atmosphere. After the addition of 340 mL of dimethyl ether (DME) and 170 mL of a 2 M sodium carbonate aqueous solution, the mixture was heat refluxed with stirring for 8 hours. After cooling the mixture to room temperature, the aqueous phase was removed. The organic phase was washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. After removing magnesium sulfate by filtration, the organic phase was concentrated. The residue was purified by silica gel column chromatography to obtain 25.0 g of the target 9-(2-formylphenyl)phenanthrene (yield: 89%).

Workup

  1. temperaturethe mixture was heat
  2. temperaturerefluxed
  3. customthe aqueous phase was removed
  4. washThe organic phase was washed with water
  5. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
  6. customAfter removing magnesium sulfate
  7. filtrationby filtration
  8. concentrationthe organic phase was concentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4efcec0fb2004ed3b49f3c052e71423e
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

Loading…