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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2179857Generated: October 31, 2026

Toluene → 9-([1,1':3',1''-Terphenyl]-5'-yl)-10-([2,2'-binaphthalen]-7-yl)anthracene

https://huagongshe.com/reaction/2179857

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPotassium Phosphate, TribasicHCID 62657—
Reactant(1~1~,2~1~:2~3~,3~1~-Terphenyl)-2~5~-ylboronic acidHCID 14739363—
Reactant9-([2,2'-Binaphthalen]-7-yl)-10-bromoanthraceneHCID 86701352—
CatalystTricyclohexylphosphineHCID 75806—
Catalyst(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumHCID 6505921—
SolventEthanolHCID 702—
Product9-([1,1':3',1''-Terphenyl]-5'-yl)-10-([2,2'-binaphthalen]-7-yl)anthraceneHCID 8670135541.6%

Reaction Steps

Under the nitrogen atmosphere, [9-([2,2′-binaphthalen]-7-yl)-10-bromoanthracene (2.0 g) as the tenth intermediate compound, [1,1′:3′,1″-terphenyl]-5′-ylboronic acid (1.0 g), Pd(dba)2 (0.03 g), tricyclohexyl phosphine (0.03 g), potassium phosphate (1.3 g), and a mixture solvent of toluene and ethanol (20 ml) (toluene/ethanol=4/1 (volume ratio)) were added to a flask and refluxed for 2 hours. Once the heating is completed, the reaction solution was cooled to room temperature. The reaction was terminated by adding water. The target compound was extracted with toluene. The solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (solvent: toluene) and also by active carbon column chromatography (solvent: toluene) to give 9-([1,1′:3′,1″-terphenyl]-5′-yl)-10-([2,2′-binaphthalen]-7-yl)anthracene (1.0 g) as the target compound represented by Formula (1-162). The scheme is shown in the following “Reaction 17”.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09070885B2
Source datasetuspto-grants-2015_06
ORD IDord-6158255d007747f1a36dd87fc4b56f0b
Source noteuspto-grants-2015_06