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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1291577Generated: October 27, 2026

5-(2,2-Dibromoethenyl)-2,2'-bithiophene → 2,2'-Bithiophene, 5-ethynyl-

https://huagongshe.com/reaction/1291577

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-(2,2-Dibromoethenyl)-2,2'-bithiopheneHCID 13113977—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
Product2,2'-Bithiophene, 5-ethynyl-HCID 645209288%

Reaction Conditions

Temperature-78 °C

Reaction Steps

Anhydrous 5-(2,2-dibromo-ethenyl)-2,2'-bithiophene was dissolved in anhydrous THF and stirred at -78° C. After n-BuLi was added into the solution and stirred for 1 hour, the temperature was raised to 25° C. and stirred for further 1 hour. The solution was monitored by thin layer chromatography to determine whether the reaction was completed. The reaction solution was then extracted with ether and washed with water. After the solution was washed with saturated NaCl solution and dried over anhydrous magnesium sulfate. After removal of ether, the crude product was purified by column chromatography and the oily product was obtained. The yield is 88%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05753692
Source datasetuspto-grants-1998_05
ORD IDord-db6b622a0ba747ffb610d1c7ba2df324
Source noteuspto-grants-1998_05