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

HRID 1506274

Reaktionsgleichung

Reaktionsgleichung von HRID 1506274
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

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 740629-Bromoanthracene

Produkt 1

HCID 2644169-(Naphthalen-2-yl)anthraceneAusbeute 173,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-37c041a24d2a49a78bc8fc470921c6ee
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09219234B2

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