Aniline → 9,9-Dimethyl-N-phenyl-9H-fluoren-2-amine

HRID 2275914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2275914
Br[C:2]1[C:14]2[C:13]([CH3:16])([CH3:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15][C:13]1([CH3:16])[C:12]2[CH:11]=[C:10]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:9]=[CH:8][C:7]=2[C:6]2[C:14]1=[CH:2][CH:3]=[CH:4][CH:5]=2

Komponenten

7

Edukt 3

HCID 6115AnilineHCID 23676156Sodium t-butoxideHCID 667979641-bromo-9,9-dimethyl-9H-fluorene

Produkt 1

HCID 187301779,9-Dimethyl-N-phenyl-9H-fluoren-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

50 g of bromo-9,9-dimethyl-9H-fluorene (183 mmol), 20 ml of aniline (220 mmol), 1.5 g of DPPF (2.7 mmol), 0.5 g of palladium(II)acetate and 45 g of sodium tert-butoxide (486 mmol) are heated at the boil in 1.5 l of toluene under a protective atmosphere for 18 h. The mixture is subsequently partitioned between toluene and water, and the organic phase is washed three times with water and dried over Na2SO4 and evaporated in a rotary evaporator. The residue which remains is recrystallised from heptane/ethyl acetate. The yield is 31.2 g (110 mmol, 52%).

Aufarbeitung

  1. customThe mixture is subsequently partitioned between toluene and water
  2. washthe organic phase is washed three times with water
  3. dry with materialdried over Na2SO4
  4. customevaporated in a rotary evaporator
  5. customThe residue which remains is recrystallised from heptane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-51723603cf6f4febaa1c485f18ed745b
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126970B2

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