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3-thiopheneethanol tubular-type preparation method and device thereof

A thiophene ethanol and tubular technology is applied in the field of tubular preparation of 3-thiophene ethanol, and can solve the problems of difficult isomer impurities and low yield, and achieve the advantages of reducing reaction time, high reaction yield and improving yield. Effect

Active Publication Date: 2015-09-09
暨明医药科技(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The final product obtained by this method contains isomer impurities that are difficult to remove, and the yield is low (Synthesis., 2008, No.11, pp 1793-1797.OrCN102241662)

Method used

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  • 3-thiopheneethanol tubular-type preparation method and device thereof
  • 3-thiopheneethanol tubular-type preparation method and device thereof
  • 3-thiopheneethanol tubular-type preparation method and device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The process parameters are as follows:

[0042] The first mixer temperature was -50°C and the second mixer temperature was 0°C.

[0043] The molar ratio of n-butyllithium to 3-bromothiophene is 1.1:1, and the molar ratio of vinyl sulfate to 3-bromothiophene is 1.1:1.

[0044] For pretreatment, 16.2Kg of 3-bromothiophene was dissolved in 90.0Kg of tetrahydrofuran to form a 3-bromothiophene solution; 13.6Kg of vinyl sulfate was dissolved in 30.0Kg of tetrahydrofuran to form a vinyl sulfate solution.

[0045] 30.3Kg n-butyllithium (2.5M n-hexane) in 0.021m 3 / s is pumped into the first mixer, while the 3-bromothiophene solution is at 0.057m 3 / s is pumped into the first mixer, and the temperature of the first mixer is -50°C. At the same time, turn on the flow pump corresponding to the vinyl sulfate solution, and the vinyl sulfate solution will flow at 0.023m 3 / s is pumped into the second mixer and mixed with the prepared 3-thiophene lithium solution, the mixing temper...

Embodiment 2

[0048] The process parameters are as follows:

[0049] The first mixer temperature was -40°C and the second mixer temperature was 10°C.

[0050] The molar ratio of n-butyllithium to 3-bromothiophene is 0.9:1, and the molar ratio of vinyl sulfate to 3-bromothiophene is 0.9:1.

[0051] Raw material pretreatment, 29.7Kg 3-bromothiophene was dissolved in 61.5Kg tetrahydrofuran to form a 3-bromothiophene solution, and 20.4Kg vinyl sulfate was dissolved in 22.5Kg tetrahydrofuran to form a vinyl sulfate solution.

[0052] 70.8Kg n-butyllithium (1.6M n-hexane) at 0.027m 3 / s is pumped into the first mixer, while the 3-bromothiophene solution is at 0.026m 3 / s pumped into the first mixer, the temperature of the first mixer is -40°C. At the same time, turn on the flow pump corresponding to the vinyl sulfate solution, and the vinyl sulfate solution will flow at 0.012m 3 / s is pumped into the second mixer and mixed with the prepared 3-thiophene lithium solution at a mixing temperature ...

Embodiment 3

[0055] The process parameters are as follows:

[0056] The first mixer temperature was -80°C and the second mixer temperature was 20°C.

[0057] The molar ratio of tert-butyllithium to 3-bromothiophene is 1.1:1, and the molar ratio of vinyl sulfate to 3-bromothiophene is 1.1:1.

[0058] Raw material pretreatment, 11.9Kg of 3-bromothiophene was dissolved in 44.0Kg of tetrahydrofuran to form a 3-bromothiophene solution, and 10.0Kg of vinyl sulfate was dissolved in 17.3Kg of tetrahydrofuran to form a vinyl sulfate solution.

[0059] 55.7Kg tert-butyllithium (1.0M n-hexane) at 0.028m 3 / s is pumped into the first mixer, while the 3-bromothiophene solution is at 0.021m 3 / s is pumped into the first mixer, and the temperature of the first mixer is -80°C. At the same time, turn on the flow pump corresponding to the vinyl sulfate solution, and the vinyl sulfate solution will flow at 0.010m 3 / s is pumped into the second mixer and mixed with the prepared 3-thiophene lithium solutio...

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Abstract

The invention provides a 3-thiopheneethanol tubular-type preparation method. According to the 3-thiopheneethanol tubular-type preparation method, an lithium alkylide solution and a 3-bromothiophene solution are delivered into a first mixer provided with a heat exchanged system at a certain ratio via different pipelines, wherein the temperature of the first mixer ranges from -30 to -120 DEG C; an obtained mixed solution and an ethylene sulfate solution in another pipeline are delivered into a second mixer for mixing and reaction, wherein the temperature of the second mixer ranges from -40 to 30 DEG C, and molar ratio of ethylene sulfate to 3-bromothiophene ranges from 0.5:1 to 2:1; a reacted liquid discharged from the second mixer is collected, and is subjected to quenching, hydrolysis, extraction, concentration, and distillation purification so as to obtain finished products. The 3-thiopheneethanol tubular-type preparation method is capable of shortening retention time of prepared 3-thiophene lithium solution effectively, shortening reaction time with the ethylene sulfate solution, reducing by-products generated via rearrangement and ring opening effectively, and increasing the maximum total yield further.

Description

technical field [0001] The invention relates to a tubular preparation method of 3-thiophenethanol and a tubular device prepared therefor, belonging to the technical field of organic synthesis. Background technique [0002] 3-Thienyl ethanol is an important intermediate in the synthesis of various chemicals, especially thienopyridines. Thienopyridine is a potent platelet aggregation inhibitor and antithrombotic drug. 3-thiophenethanol is a key intermediate in the synthesis of oligothiophene with anti-cancer imaging function. In addition to its important role in the pharmaceutical industry, in the research of new composite materials, 3-thiophenethanol is also a research hotspot, which can be used to synthesize conductive composite materials and self-doping nanocomposite materials. With the continuous development of downstream products, the synthesis of 3-thiophenethanol has also attracted much attention. [0003] At present, there are few reported methods for preparing thio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/16
CPCC07D333/16
Inventor 何牧陈剑戈张喜通
Owner 暨明医药科技(苏州)有限公司
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