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HRID 2091440Erstellt: 26. Oktober 2026

Toluene → N4,N4,N4'-Triphenyl-[1,1'-biphenyl]-4,4'-diamine

https://huagongshe.com/reaction/2091440

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTolueneHCID 1140—
EduktPotassium Phosphate, TribasicHCID 62657—
Edukt4-BromodiphenylamineHCID 6425786—
Edukt4-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)HCID 12166934—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
Katalysator2-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11269872—
LösungsmittelWaterHCID 962—
ProduktN4,N4,N4'-Triphenyl-[1,1'-biphenyl]-4,4'-diamineHCID 2201329581,4%

Reaktionsschritte

4-(diphenylamino)phenylboronic acid (4.87 g, 16.8 mmol), 4-bromo-N-phenylaniline (3.5 g, 14 mmol), potassium phosphate (9.2 g, 42 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.23 g, 0.56 mmol) were added to a three-neck flask under nitrogen. 200 mL of toluene and 20 mL of water was then added. The solution was degassed with nitrogen for 20 minutes. Pd2(dba)3 (0.13 g, 0.14 mmol) was added to the mixture. The mixture was then heated up to reflux overnight. After cooled to room temperature, the organic layer was separated and dried over magnesium sulfate. After evaporating solvent, the residue was purified by column chromatography using 1:2 dichloromethane and hexanes as eluent. 4.7 g of desired product was obtained. (81% yield)

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08440326B2
Quelldatensatzuspto-grants-2013_05
ORD IDord-e54bba8890714effaf8a5159aeabcd93
Quellennotizuspto-grants-2013_05