ChemicalBook CAS DataBase List [1,1':2',1''-Terphenyl]-4-amine (9CI)

[1,1':2',1''-Terphenyl]-4-amine (9CI) synthesis

4synthesis methods

Product Name:[1,1':2',1''-Terphenyl]-4-amine (9CI)
CAS Number:5728-65-4
Molecular formula:C18H15N
Molecular Weight:245.32

2052-07-5 Synthesis

2052-07-5
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5728-65-4
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Yield:5728-65-4 67%

Reaction Conditions:

with tetrakis-(triphenylphosphine)-palladium;potassium carbonate in ethanol;lithium hydroxide monohydrate;toluene at 80; for 18 h;Inert atmosphere;

Steps:

1.1 Intermediate A was synthesized by Reaction Scheme 1-1 below:

In an argon atmosphere, in a 2 L three-neck flask, 2-bromobiphenyl (35.0 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (49.3 g), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄, 8.7 g), and potassium carbonate (K₂CO₃, 41.5 g) were added and dissolved in a mixed solvent of toluene, water, and ethanol (10:2:1, 600 mL), and the mixture was heated and stirred at about 80° C. for about 18 hours. The resultant mixture was extracted with dichloromethane (CH₂Cl₂) by adding water to obtain organic layers. The obtained organic layers were combined and dried over magnesium sulfate (MgSO₄), and the solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain Intermediate A (24.8 g, yield: 67%). The molecular weight of Intermediate A measured by FAB-MS measurement was 245.

References:

US2022/131079,2022,A1 Location in patent:Paragraph 0204-0207