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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1775389Generated: November 2, 2026

Ethanol → 1-Bromo-6-(naphthalen-1-yl)pyrene

https://huagongshe.com/reaction/1775389

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantSodium CarbonateHCID 10340—
ReactantPyrene, 1,6-Dibromo-HCID 176470—
Reactant1-Naphthaleneboronic acidHCID 254532—
CatalystHCID 178418397HCID 178418397—
SolventTolueneHCID 1140—
Product1-Bromo-6-(naphthalen-1-yl)pyreneHCID 8608412445.5%

Reaction Conditions

Temperature90 °C

Reaction Steps

A mixture of 27.2 g (75.6 mmol) of 1,6-dibromopyrene, 13 g (75.6 mmol) of naphthalen-1-ylboronic acid, 0.87 g(0.756 mmol) of Tetrakis(triphenylphosphine)Palladium, 57 ml of 2M Na2CO3, 120 ml of EtOH and 300 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 24 h. After the reaction finish, the mixture was allowed to cool to room temperature. Than 500 ml MeOH was added, while stirring and the precipitated product was filtered off with suction. To give 14 g (yield 45.5%) of beige product which was recrystallized from 1,4-Dioxane.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09260363B2
Source datasetuspto-grants-2016_02
ORD IDord-251a535525a94d809a2b0f1bae077b16
Source noteuspto-grants-2016_02