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

HRID 1506274

Reaction equation

HRID 1506274 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+]>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.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

6

Reactant 3

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 740629-Bromoanthracene

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

22.5 g of 9-bromoanthracene, 15.8 g of 2-naphthelene boronic acid and 2.0 g of tetrakis(triphenylphosphine)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-37c041a24d2a49a78bc8fc470921c6ee
Source dataset
uspto-grants-2015_12
Patent number
US09219234B2

Linked notes

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