Synthesis method of 1,2-di(2-thienyl)ethane

Abstract

The invention relates to a synthesis method of 1,2-di(2-thienyl)ethane, and particularly relates to a synthesis method of 1,2-di(2-thienyl)ethane by firstly converting 2-penphene as a raw material into thienyl borane, then reacting with p-toluene sulfonate-2-(2-thienyl)ethyl to generate 1,2--di(2-thienyl)ethane. The 1,2-di(2-thienyl)ethane is synthesized by the following steps: by taking 2-penphene as a raw material, firstly converting into thienyl borane, then reacting with p-toluene sulfonate-2-(2-thienyl)ethyl to generate 1,2--di(2-thienyl)ethane. The invention provides a new method for synthesizing 1,2-di(2-thienyl)ethane, and the synthesis method has the characteristics of being mild in reaction conditions, short in reaction route, and high in reaction yield.

Description

technical field [0001] The present invention relates to a kind of synthetic method of 1,2-bis(2-thienyl)ethane, especially a kind of 2-chlorothiophene is used as raw material to change trithienyl borane first, and then with p-toluenesulfonic acid-2 - (2-thienyl) ethyl ester reaction to generate 1,2-bis (2-thienyl) ethane synthesis method. Background technique [0002] 1,2-bis(2-thienyl)ethane is a fine chemical intermediate, and many researchers have studied its synthesis. The earliest literature report appeared in J. Am. Chem. Soc, 1942, 64(3):P 477-480 Above, the author used 2-chloromethylthiophene as a raw material to produce 1,2-bis(2-thienyl)ethane in the presence of magnesium by adding ethylene oxide for condensation reaction with a yield of 69%; similar The method also appears in the journal Polymer, 2000, 41:P 5681-5687 In the above, the researchers used two molecules of 2-chloromethylthiophene to undergo condensation reaction in the presence of magnesium to gener...

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Problems solved by technology

The earliest literature report appeared in J. Am. Chem. Soc, 1942, 64(3):P477-480, the author used 2-chloromethylthiophene as raw material, passed through in the presence of magnesium Add ethylene oxide for condensation reaction to produce 1,2-di(2-thienyl)ethane with a yield of 69%; a similar method also appeared in the journal Polymer, 2000, 41:P5681-5687 , the researchers used two molecules of 2-chloromethylthiophene to conduct a condensation reaction in the presence of magnesium to generate one molecule of 1,2-bis(2-thienyl)ethane with a yield of 58%; the above Although the preparation of the two methods is relatively simple, the production yield of the raw material 2-chloromethylthiophene used in the preparation is generally low (about 40%), resulting in a total yield of 27.6% and 23.2%, respectively, not exceeding 30%. %. In addition, there is a journal J. Org. Chem, 1976, 41 (12): P2187-2193 reported that N-(1-(2-thienyl)-2-thienyl ) Dimethylamine reacts with methyl iodide to obtain the corresponding quaternary ammonium salt, and then reduces it to obtain 1,2-bis(2-thienyl)ethane, the yield of the two-step reaction is as low as 10%. However, the journal Chemistry Letters, 1981: P627-630 reported the preparation of 1,2-bis(2-thienyl) by organic selenide The method of ethane, the yield reached 32%; the latest literature report comes from Macromolecules, 2011, 44:P4711-4720, the author uses 2-chloromethylthiophene as raw material, through Wurtz reaction 1,2-bis(2-thienyl)ethane was produced in only 20% yield