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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1027319Generated: October 26, 2026

Dimethylformamide → 1,3,6-Tri(4-methylphenyl)pyrene

https://huagongshe.com/reaction/1027319

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium Phosphate, TribasicHCID 62657—
ReactantTolylboronic acidHCID 79799—
Reactant1,3,6-TribromopyreneHCID 3015969—
CatalystTetrabutylammonium BromideHCID 74236—
Catalystpalladium(II) acetateHCID 167845—
SolventWaterHCID 962—
Product1,3,6-Tri(4-methylphenyl)pyreneHCID 86628591167.2%

Reaction Conditions

Temperature130 °C

Reaction Steps

Next, a mixed solution of 2.0 g of 1,3,6-tribromopyrene, 2.5 g of 4-methylphenylboronic acid, 5.8 g of tripotassium phosphate, 0.88 g of tetrabutylammonium bromide, 61 mg of palladium acetate and 137 ml of deaerated dimethylformamide was heated with stirring under a nitrogen gas flow at 130° C. for 9 hours. After cooling to room temperature, 800 ml of water was injected, followed by extraction with 200 ml of dichloromethane. The organic layer was washed twice with 100 ml of water, dried over magnesium sulfate and then evaporated. The resultant concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 1.8 g of 1,3,6-tri(4-methylphenyl)pyrene as a pale yellow powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08729530B2
Source datasetuspto-grants-2014_05
ORD IDord-e068d6f8c028407fb4c7585fa03d15f9
Source noteuspto-grants-2014_05