Phenyl-1-naphthylamine → N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine

HRID 1968378

Reaktionsgleichung

Reaktionsgleichung von HRID 1968378
[C:1]1([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=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.Cl[Pd]Cl.[Fe+2]>[Br:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[CH:23]=[CH:24][C:19]([N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH:11]=[CH:10][CH:9]=3)=[CH:20][CH:21]=2)=[CH:26][CH:27]=1

Komponenten

6

Edukt 3

HCID 7013Phenyl-1-naphthylamineHCID 71104,4'-DibromobiphenylHCID 23676156Sodium t-butoxide

Produkt 1

HCID 16755312N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of N-phenylnaphthalen-1-amine (4.41 g, 20 mmol), 4,4′-dibromo-1,1′-biphenyl (15 g, 48 mmol), sodium tert-butoxide (4.8 g, 50 mmol) and Pd(dppf)Cl2 (0.44 g, 0.6 mmol) in anhydrous toluene (100 ml) was degassed and heated at 80° C. for 10 hours. After cooling to RT, the mixture was poured into dichloromethane (400 ml) and stirred for 30 min, then washed with brine (100 ml). The organic is collected and dried over Na2SO4, loaded on silica gel, and purified by flash column (hexanes to hexanes/ethyl acetate 90:1) to give a solid which was washed with methanol and dried under air to give a white solid 4 (5.58 g, in 62% yield).

Aufarbeitung

  1. customwas degassed
  2. temperatureAfter cooling to RT
  3. additionthe mixture was poured into dichloromethane (400 ml)
  4. washwashed with brine (100 ml)
  5. customThe organic is collected
  6. dry with materialdried over Na2SO4
  7. custompurified by flash column (hexanes to hexanes/ethyl acetate 90:1)
  8. customto give a solid which
  9. washwas washed with methanol
  10. customdried under air

Quellen und Nachweise

ORD-Eintrag
ord-84ed204c9dde47e9afa4c74109b916e3
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426040B2

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