Sodium Carbonate → 9-(Naphthalen-2-yl)anthracene

HRID 534811Notes

Reaction equation

HRID 534811 reaction equation
Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH:4]1[C:3]2[C:2](=[CH:15][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][C:4]=1[C:3]1[C:2]2[C:11]([CH:10]=[C:9]3[C:8]=1[CH:7]=[CH:7][CH:6]=[CH:5]3)=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 740629-Bromoanthracene

Product 1

HCID 2644169-(Naphthalen-2-yl)anthraceneYield 173.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

22.5 g of 9-bromoanthracene, 15.8 g of 2-naphthelene boronic acid and 2.0 g of tetrakis(triphenylphophine)palladium were mixed, followed by argon displacement. After adding 150 ml of toluene and 140 ml of 2M sodiumcarbonate aqueous solution thereto, it was refluxed on heating for 7 hours. After standing to cool, the crystal precipitated was filtrated it was washed by ethanol and toluene. The crystal obtained was recrystallized in toluene, followed by filtering and drying, and then 23.1 g of 9-(naphthalene-2-yl)anthracene was obtained (yield: 87%).

Workup

  1. temperatureit was refluxed
  2. temperatureon heating for 7 hours
  3. temperatureto cool
  4. customthe crystal precipitated
  5. filtrationwas filtrated it
  6. washwas washed by ethanol and toluene
  7. customThe crystal obtained
  8. customwas recrystallized in toluene
  9. filtrationby filtering
  10. customdrying

Sources & evidence

ORD record
ord-3786fd58829b4418912ab428e35d8e12
Source dataset
uspto-grants-2014_10
Patent number
US08853675B2

Reaction notes

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