Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1662909Generated: October 29, 2026

Toluene → HCID 23110736, compound

https://huagongshe.com/reaction/1662909

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantSodium CarbonateHCID 10340—
Reactant1,4-DibromonaphthaleneHCID 66521—
Reactant(Naphthalen-2-yl)boronic acidHCID 2734375—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductHCID 23110736HCID 2311073625.3%

Reaction Conditions

Temperature78 °C

Reaction Steps

Under an argon gas atmosphere, 121 g (700 mmol) of 2-naphthaleneboronic acid, 200.0 g (700 mmol) of 1,4-dibromonaphthalene, 16.2 g (13.4 mmol) of tetrakis(triphenylphosphine) palladium(0), 3.0L of toluene, 3.2L of dimethoxyethane and 1.60L of 2M sodium carbonate solution were mixed, and stirred for 20 hours at 78 degrees C. The reaction mixture experienced filtration to be subsequently cleansed by water and methanol. The obtained solid was added with toluene to be heat-dissolved. Insoluble matter therein was eliminated by filtration, such that the filtrate was distilled away under reduced pressure. By recrystallizing residue by toluene and hexane, 59 g of 4-bromo-1-(2-naphthyl)naphthalene was obtained at an yield of 25%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08034256B2
Source datasetuspto-grants-2011_10
ORD IDord-5ff77ae854f54163988156824c1b5af5
Source noteuspto-grants-2011_10