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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 600161Generated: October 25, 2026

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

https://huagongshe.com/reaction/600161

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

A mixed solution of 2 g of the above-mentioned 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 while stirred under nitrogen gas stream at a temperature of 130° C. for 9 hours. After cooling the mixed solution to room temperature, 800 ml of water was injected thereinto to extract therefrom with 200 ml of dichloromethane. The organic layer was washed twice with 100 ml of water, dried by magnesium sulfate and thereafter concentrated by evaporation. The organic layer was purified by silica gel column chromatography and thereafter vacuum dried under a temperature of 70° C. to obtain 1.8 g of 1,3,6-tri(4-methylphenyl)pyrene as pale-yellow powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07901794B2
Source datasetuspto-grants-2011_03
ORD IDord-0d6aab9930a54f03800ebe17ab49de3d
Source noteuspto-grants-2011_03