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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1965883Generated: October 30, 2026

Toluene → 5-(7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde

https://huagongshe.com/reaction/1965883

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPotassium CarbonateHCID 11430—
Reactant5-Formyl-2-thiopheneboronic acidHCID 2773430—
Reactant(7-bromo-9H-fluoren-2-yl)-dibutyl amineHCID 59325934—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
SolventMethanolHCID 887—
Product5-(7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehydeHCID 86641778—

Reaction Conditions

Temperature60 °C

Reaction Steps

Under N2 atmosphere, 0.37 parts of (7-bromo-9H-fluoren-2-yl)-dibutyl amine (11), 0.19 parts of 5-formyl-2-thiopheneboronic acid, 0.41 parts of potassium carbonate, and 0.16 parts of PdCl2(dppf) were added into 5 parts of toluene and 5 parts of CH3OH, followed by stirring and mixing. Then, the reaction mixture was heated to 60° C. and reacted for 18 hours. After the reaction mixture was quenched by water, using the diethyl ether to extract the product, and magnesium sulfate was used for dehydration. After removing the solvent, the residual was purified with chromatography method column by using dichloromethane/hexane co-solvent as an eluent, to obtain a compound (12a) of the present example. This compound was in a form of a tangerine solid, and the yield of this compound was 61%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08419808B2
Source datasetuspto-grants-2013_04
ORD IDord-d74ca7c5d40c4def994e9e7e16f9f8c7
Source noteuspto-grants-2013_04