CN102363614B - Method for synthesizing 2-bromothiophene - Google Patents
Method for synthesizing 2-bromothiophene Download PDFInfo
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- CN102363614B CN102363614B CN 201110359145 CN201110359145A CN102363614B CN 102363614 B CN102363614 B CN 102363614B CN 201110359145 CN201110359145 CN 201110359145 CN 201110359145 A CN201110359145 A CN 201110359145A CN 102363614 B CN102363614 B CN 102363614B
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- waste water
- bromothiophene
- hydrogen peroxide
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- thiophene
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Abstract
The invention discloses a method for synthesizing 2-bromothiophene, which is characterized by comprising the following steps: adding bromine-containing waste water into a reactor, wherein the waste water is waste water produced in downstream production of 2-bromothiophene, the main content of the waste water is magnesium bromide, the magnesium bromide mass content in the bromine-containing waste water is 5 to 15 percent; adding thiophene and concentrated sulfuric acid into bromine-containing waste water, keeping the temperature between 4 and 6 DEG C, slowly adding hydrogen peroxide, continuing to keep the temperature for 1 to 3 hours after the addition of hydrogen peroxide is finished, standing and demixing; and distilling an organic material under reduced pressure to obtain 2-bromothiophene. The mass ratio of bromine-containing waste water to thiophene to concentrated sulfuric acid to hydrogen peroxide is 500:(35-45):(55-70):(120-150). The method disclosed by the invention has the advantages that: the raw materials are cheap and readily available and has small toxicity; the selectivity of chemical reactions is high; the yield is high; the product quality is high; brominating agent can be recycled; and the like.
Description
Technical field
The present invention relates to a kind of synthetic method of organic synthesis intermediate 2-bromothiophene.
Background technology
The 2-bromothiophene is intermediate important in organic synthesis, be widely used in the fields such as medicine, agricultural chemicals, macromolecular material, especially at field of medicaments, the 2-bromothiophene is the raw material of synthesizing thiofuran ethamine, for the synthesis of the medicine of the therapeutic cerebrovascular diseases such as Ticlopidine, pyrimidone derivatives, inhibition acquired immune deficiency syndrome (AIDS) and correlated virus thereof, demand is increasing.
the synthetic 2-bromothiophene of document record, adopt respectively the glacial acetic acid solvent method, the carbon tetrachloride solvent method, direct bromination has synthesized the 2-bromothiophene, high spot reviews add the bromine mode, add the bromine time, proportioning raw materials, the influence factors such as temperature of reaction are produced the impact of 2-bromothiophene technique on direct bromination, and the production cost of three kinds of production technique has been carried out comparative analysis. experimental result shows: glacial acetic acid solvent method and carbon tetrachloride solvent method are not suitable for suitability for industrialized production, and direct bromination is that thiophene is dissolved in acetic acid, below 10 ℃, the glacial acetic acid solution of bromine is being added.Add water to reaction mixture again, separate out oily liquids.Use extracted with diethyl ether.Add salt of wormwood and remove acetic acid in extraction liquid, drying boils off ether, then carries out underpressure distillation, collects 42-46 ℃ of (1.73kPa) cut, namely gets the 2-bromothiophene, productive rate 55%.The productive rate of direct bromination is very low.
Summary of the invention
[0004] technical problem to be solved by this invention is for the deficiencies in the prior art, and the synthetic method of more reasonable, the workable 2-bromothiophene of a kind of method is provided.
Technical problem to be solved by this invention is to realize by following technical scheme.The present invention is a kind of synthetic method of 2-bromothiophene, is characterized in, its step is as follows:
Add brominated waste water in reaction vessel, the waste water that this wastewater source produces in the downstream production of 2-bromothiophene, major ingredient is magnesium bromine salt; In brominated waste water, the mass content of magnesium bromide is 5-15%; Add thiophene in brominated waste water, the vitriol oil is controlled 4-6 ℃ of temperature, slowly drips hydrogen peroxide, finishes and continues insulation 1-3 hour, standing demix; The organic layer underpressure distillation obtains the 2-bromothiophene;
The mass ratio of described brominated waste water, thiophene, the vitriol oil and hydrogen peroxide is 500:35-45:55-70:120-150.
In the synthetic method technical scheme of above-described 2-bromothiophene: the mass ratio of described brominated waste water, thiophene, the vitriol oil and hydrogen peroxide is preferably 500:38.5:64:137.
The synthetic route of the synthetic method of 2-bromothiophene of the present invention is as follows:
Compared with prior art, the raw material of the inventive method is cheap and easy to get, toxicity is little, selectivity of chemical equation is high, yield is high, good product quality, the bromizating agent recoverable.
Embodiment
Below further describe concrete technical scheme of the present invention, so that those skilled in the art understands the present invention further, and do not consist of its Copyright law.
Embodiment 1, a kind of synthetic method of 2-bromothiophene, and its step is as follows:
Add brominated waste water in reaction vessel, the waste water that this wastewater source produces in the downstream production of 2-bromothiophene, major ingredient is magnesium bromine salt; In brominated waste water, the mass content of magnesium bromide is 5%; Add thiophene in brominated waste water, the vitriol oil is controlled 4 ℃ of temperature, slowly drips hydrogen peroxide, finishes and continues insulation 1 hour, standing demix; The organic layer underpressure distillation obtains the 2-bromothiophene;
The mass ratio of described brominated waste water, thiophene, the vitriol oil and hydrogen peroxide is 500:35:55:120.
Embodiment 2, a kind of synthetic method of 2-bromothiophene, and its step is as follows:
Add brominated waste water in reaction vessel, the waste water that this wastewater source produces in the downstream production of 2-bromothiophene, major ingredient is magnesium bromine salt; In brominated waste water, the mass content of magnesium bromide is 15%; Add thiophene in brominated waste water, the vitriol oil is controlled 6 ℃ of temperature, slowly drips hydrogen peroxide, finishes and continues insulation 3 hours, standing demix; The organic layer underpressure distillation obtains the 2-bromothiophene;
The mass ratio of described brominated waste water, thiophene, the vitriol oil and hydrogen peroxide is 500:45:70:150.
Embodiment 3, a kind of synthetic method experiment of 2-bromothiophene, and step is as follows:
Add the brominated waste water (waste water that this wastewater source produces in the downstream production of 2-bromothiophene in the there-necked flask of 500ml, mainly magnesium bromine salt) 500 grams, convert as magnesium bromide content is 40 grams, add thiophene 38.5 grams (0.4583mol), the vitriol oil 64 grams, control 5 ℃ of temperature, slowly drip hydrogen peroxide 137 grams, finish and continue insulation 1 hour, standing demix, the organic layer underpressure distillation obtains 2-bromothiophene 65.74 grams (0.402mol), content 99.62%, yield 88%.
Claims (1)
1. the synthetic method of a 2-bromothiophene, is characterized in that, its step is as follows:
Add brominated waste water in reaction vessel, the waste water that this wastewater source produces in the downstream production of 2-bromothiophene, major ingredient is magnesium bromine salt; In brominated waste water, the mass content of magnesium bromide is 5-15%; Add thiophene in brominated waste water, the vitriol oil is controlled 4-6 ℃ of temperature, slowly drips hydrogen peroxide, finishes and continues insulation 1-3 hour, standing demix; The organic layer underpressure distillation obtains the 2-bromothiophene; The mass ratio of described brominated waste water, thiophene, the vitriol oil and hydrogen peroxide is 500:38.5:64:137.
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| Application Number | Priority Date | Filing Date | Title |
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| CN 201110359145 CN102363614B (en) | 2011-11-14 | 2011-11-14 | Method for synthesizing 2-bromothiophene |
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| CN 201110359145 CN102363614B (en) | 2011-11-14 | 2011-11-14 | Method for synthesizing 2-bromothiophene |
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| CN102363614A CN102363614A (en) | 2012-02-29 |
| CN102363614B true CN102363614B (en) | 2013-06-12 |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107935985A (en) * | 2017-12-25 | 2018-04-20 | 中山市得高行知识产权中心（有限合伙） | A kind of synthetic method of 2 bromothiophene |
| CN111763194B (en) * | 2020-07-09 | 2021-09-21 | 浙江燎原药业股份有限公司 | Preparation method of 2-bromothiophene |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101885720A (en) * | 2010-07-19 | 2010-11-17 | 连云港宏业化工有限公司 | Method for synthesizing 2-thiophene ethylamine |
| CN102093256A (en) * | 2010-12-22 | 2011-06-15 | 浙江吉华集团有限公司 | Synthesis method of 2,4-binitro-6-bromaniline diazonium salt |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101885720A (en) * | 2010-07-19 | 2010-11-17 | 连云港宏业化工有限公司 | Method for synthesizing 2-thiophene ethylamine |
| CN102093256A (en) * | 2010-12-22 | 2011-06-15 | 浙江吉华集团有限公司 | Synthesis method of 2,4-binitro-6-bromaniline diazonium salt |
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Effective date of registration: 20210430 Address after: 222523 duigougang Town, Guannan County, Lianyungang City, Jiangsu Province (Chemical Industrial Park) Patentee after: JIANGSU DIPU TECHNOLOGY Co.,Ltd. Address before: 222500 duigougang Town, Guannan County, Lianyungang City, Jiangsu Province (Chemical Industrial Park) Patentee before: LIANYUNGANG HONGYE CHEMICAL Co.,Ltd. |
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