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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2285340Generated: October 31, 2026

Tris(2-methoxyphenyl)phosphine → 1,6-Di(quinolin-8-yl)pyrene

https://huagongshe.com/reaction/2285340

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTris(2-methoxyphenyl)phosphineHCID 78464—
Reactant8-Quinolineboronic acidHCID 2734380—
ReactantSodium Carbonate MonohydrateHCID 2735133—
Reactant2,7-DibromopyreneHCID 13615479—
ReactantTricaprylylmethyl ammonium chlorideHCID 77620884—
CatalystTrioctylmethylammonium chlorideHCID 21218—
Catalystpalladium(II) acetateHCID 167845—
SolventTolueneHCID 1140—
Product1,6-Di(quinolin-8-yl)pyreneHCID 8671172448%

Reaction Conditions

Temperature100 °C

Reaction Steps

Quinoline-8-boronic acid (2.2 g, 12.2 mmol), trioctylmethylammonium chloride (trademark name: Aliquat336 (hereinafter referred to as Aliquat336), prepared by Aldrich Corporation, 0.74 g), palladium acetate (1.3 mg), tris(o-methoxyphenyl)phosphine (13.3 mg), toluene (58 ml), and sodium carbonate water solution (17.8 mmol) were added to dibromo pyrene (2.0 g, 5.6 mmol) synthesized in the prepared example and they were agitated at a temperature of 100° C. of four hours. A crystal was obtained by cooling the resultant reaction liquid at room temperature and filtering the cooled reaction (including the crystal). The compound B of 1.8 g was obtained by washing the crystal in an order of toluene, water, and methanol, and drying the washed crystal under reduced pressure (yield 48%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09147846B2
Source datasetuspto-grants-2015_09
ORD IDord-22f685f4ef5a431a95a086a1047537dc
Source noteuspto-grants-2015_09