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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1525375Generated: November 2, 2026

Dimethylformamide → Ethyl ([1~2~,2~2~:2~5~,3~2~-terthiophen]-2~3~-yl)acetate

https://huagongshe.com/reaction/1525375

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant2-(Tri-n-butylstannyl)thiopheneHCID 2779373—
ReactantHCID 11209627HCID 11209627—
CatalystHCID 178418476HCID 178418476—
SolventWaterHCID 962—
ProductEthyl ([1~2~,2~2~:2~5~,3~2~-terthiophen]-2~3~-yl)acetateHCID 5805179385%

Reaction Conditions

Temperature100 °C

Reaction Steps

The synthesis of 3T-ET is carried by first synthesizing ethyl 2-(2,5-dibromothiophen-3-yl)acetate using known methods and is performed as follows. Ethyl 2-(2,5-dibromothiophen-3-yl)acetate (6.4 g, 10 mmol) and 2-(tributylstannyl)thiophene (15 g, 20 mmol) are added to a 30 mL dry DMF solution of dichlorobis-(triphenylphosphine)palladium (1.3 g, 1.5 mmol). After three freeze thaw cycles, the mixture is heated at 100° C. for 48 hours. The mixture is cooled to room temperature and poured into a beaker containing 150 mL of water and subsequently extracted with CH2Cl2. The extracted CH2Cl2 mixture is dried with Na2SO4. After filtering and evaporation of solvent, the crude product is purified by chromatography on silica gel using toluene as eluent. The final product is obtained in 85% yield as pale yellow oil. The characterization of the compound is consistent with that published in the literature.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09079999B2
Source datasetuspto-grants-2015_07
ORD IDord-0bf6c1fb5e05468b95bca37191ae4154
Source noteuspto-grants-2015_07