Bromobenzene → N~1~,N~1~,N~5~-Triphenylnaphthalene-1,5-diamine

HRID 22622

Reaktionsgleichung

[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([NH2:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(P([C:29]([CH3:32])([CH3:31])C)C(C)(C)C)(C)(C)C.C[C:34]([CH3:37])([O-])[CH3:35].[Na+]>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C1(C)C(C)=CC=CC=1>[C:14]1([N:1]([C:31]2[CH:29]=[CH:32][CH:6]=[CH:5][CH:4]=2)[C:2]2[C:11]3[C:6](=[C:7]([NH:12][C:35]4[CH:34]=[CH:37][CH:11]=[CH:2][CH:3]=4)[CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][CH:3]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

1,5-Diaminonaphthalene (16.0 g, 0.101 mol) was combined with bromobenzene (47.1 g, 0.300 mol), palladium diacetate (1.2 g, 0.004 mol), tri-t-butylphosphine (4 mL), sodium t-butoxide (24.0 g, 0.26 mol), and xylene (400 mL). The mixture was heated at 140° C. with magnetic stirring under a nitrogen atmosphere. After 15 h, an additional amount of palladium diacetate (0.100 g, 0.0004 mol) was added. After heating for another 6 h, an additional amount of palladium diacetate (0.100 g, 0.0004 mol) was added. After heating for another 15 h the heat was removed. After cooling to room temperature, the solid present was filtered off and the filtrate was purified by column chromatography. This afforded 6.0 g (15% yield) of N,N,N′-triphenyl-1,5-diaminonaphthalene.

Aufarbeitung

temperatureAfter heating for another 6 h
temperatureAfter heating for another 15 h the heat
customwas removed
temperatureAfter cooling to room temperature
filtrationthe solid present was filtered off
customthe filtrate was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-d30650a7d9c94a198aefea829969b8d9
Quelldatensatz: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06849345B2

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