4,4'-Dibromobiphenyl → 4,4'-Bis(9H-carbazol-9-yl)biphenyl

HRID 590007

Reaktionsgleichung

Reaktionsgleichung von HRID 590007
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+:16]>C(Cl)(Cl)Cl>[CH:3]1[C:4]2[N:16]([C:11]3[CH:12]=[CH:13][C:8]([C:5]4[CH:6]=[CH:7][C:2]([N:16]5[C:13]6[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=6[C:5]6[C:4]5=[CH:3][CH:2]=[CH:7][CH:6]=6)=[CH:3][CH:4]=4)=[CH:9][CH:10]=3)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:5]=2[CH:6]=[CH:7][CH:2]=1

Komponenten

4

Edukt 2

HCID 71104,4'-DibromobiphenylHCID 25517Ammonium Chloride

Produkt 1

HCID 112487164,4'-Bis(9H-carbazol-9-yl)biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

The reaction was conducted for 15 minutes in the same experimental procedures as in Example 16 except for using 4,4′-dibromobiphenyl (9.8 g, 31.6 mol, 1.0 equivalent) as an aryl halide. To the reaction mixture was added an aqueous solution of ammonium chloride, and the mixture was poured into chloroform (500 mL). The aqueous layer was separated off, and the organic layer was passed through a silica gel pad and concentrated to remove the excess chloroform under reduced pressure. To the thus-obtained suspension was added methanol (150 mL), and the crystal was collected from the suspension by suction filtration, washed with methanol and dried under reduced pressure to afford 14.9 g of CBP as a pale yellow powder.

Aufarbeitung

  1. customThe aqueous layer was separated off
  2. concentrationconcentrated
  3. customto remove the excess chloroform under reduced pressure
  4. additionTo the thus-obtained suspension was added methanol (150 mL)
  5. filtrationthe crystal was collected from the suspension by suction filtration
  6. washwashed with methanol
  7. customdried under reduced pressure
  8. customto afford 14.9 g of CBP as a pale yellow powder

Quellen und Nachweise

ORD-Eintrag
ord-2f25c1b080d748979dcb27aabff56475
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233922B2

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