CN106632175A - Preparation method of ethyl 5-bromo-2-furoate - Google Patents
Preparation method of ethyl 5-bromo-2-furoate Download PDFInfo
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- CN106632175A CN106632175A CN201611037801.0A CN201611037801A CN106632175A CN 106632175 A CN106632175 A CN 106632175A CN 201611037801 A CN201611037801 A CN 201611037801A CN 106632175 A CN106632175 A CN 106632175A
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- bromo
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- ethanol
- rotary evaporation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Abstract
The invention relates to a preparation method of ethyl 5-bromo-2-furoate. The preparation method comprises following steps: furoic acid and ethanol are mixed and stirred in a certain ratio, heated to 60-80 DEG C and subjected to refluxing until the components are completely dissolved, thionyl chloride is added proportionally and is dripped off within 1-4 h, a mixture is subjected to refluxing continuously for 5-8 h, and the reaction is ended; the mixture is subjected to rotary evaporation and concentration, and ethanol is recycled; remaining concentrate is diluted with water, extracted with n-hexane, washed with a weak base solution and a saturated salt solution, dried with anhydrous sodium sulfate and subjected to rotary evaporation and concentration, and a pure product of ethyl 5-bromo-2-furoate is obtained. The preparation method has the advantages as follows: reaction raw materials are relatively available, the price is reasonable, reaction conditions are mild, operation and control are easy, post-treatment is simple, and besides, the product is stable in quality and high in purity.
Description
Technical field
The invention belongs to organic synthesis field, and in particular to a kind of preparation method of the bromo- 2- ethyl furoates of 5-.
Background technology
The bromo- 2- ethyl furoates of 5- are the important intermediates of organic synthesis, are mainly used in medicine intermediate, organic synthesis,
Can be applicable to the aspects such as pesticide producing.
The content of the invention
It is for prior art that the present invention needs the problem for solving, there is provided a kind of process is simple is reasonable, low cost, and product is pure
Degree is high, is suitable to the preparation method of the bromo- 2- ethyl furoates of the 5- in laboratory and industrialized production.
The present invention is achieved through the following technical solutions：
A kind of preparation method of the bromo- 2- ethyl furoates of 5-, it is characterized in that：Comprise the following steps：
Furancarboxylic acid and ethanol are mixed and stirred for according to certain ratio, are heated to 60 DEG C -80 DEG C and are back to be completely dissolved, according to one
Certainty ratio adds thionyl chloride, 1-4 hours to drip off, and continues the 5-8 hours that flow back, and reaction terminates.Rotary evaporation is concentrated, and reclaims second
Alcohol.Remaining concentrate is diluted with water, n-hexane extraction, respectively with weak caustic solution and saturated common salt water washing, anhydrous sodium sulfate is done
It is dry, obtain the bromo- 2- ethyl furoates sterlings of 5- after rotary evaporation concentration.
The preparation method of the bromo- 2- ethyl furoates of 5- of the present invention, ethanol is both reactant and solvent.
The preparation method of the bromo- 2- ethyl furoates of 5- of the present invention, furancarboxylic acid is 1 with the molar ratio of thionyl chloride：1.5-1：
3。
The preparation method of the bromo- 2- ethyl furoates of 5- of the present invention, alkali is sodium acid carbonate, sodium carbonate, saleratus, potassium carbonate
One kind.
The preparation method of the bromo- 2- ethyl furoates of 5- of the present invention, is heated to reflux temperature 60-80 DEG C, reflux time 5-8
Hour, thionyl chloride time for adding 1-4 hours.
Ethanol is absolute ethyl alcohol.Saturated aqueous common salt weight concentration is 26.5%.
The synthesis technique and synthesis step of the bromo- 2- ethyl furoates of 5- of the present invention is as follows：
Beneficial effects of the present invention：Reaction raw materials are relatively easy to get, and reasonable price, reaction condition is gentle, it is easy to operate, it is easy to control
System, post processing is simple, and product quality is stable, and purity is high.
Specific embodiment
Embodiment 1：
By furancarboxylic acid（100g,0.526mol）Add ethanol (600mL) simultaneously to stir, be warming up to 70 DEG C and be back to and be completely dissolved, be added dropwise
Thionyl chloride (188g, 1.579mol), dripped off at 4 hours, continued to flow back 4 hours, and reaction terminates.Rotary evaporation is concentrated, and is reclaimed
Ethanol.Remaining concentrate dilute with water, n-hexane (3 × 300mL) extraction, merge organic phase after respectively with 5% sodium carbonate liquor,
Saturated common salt water washing, anhydrous sodium sulfate drying, filtration obtain the bromo- 2- ethyl furoates sterlings of 5- after the concentration of filtrate rotary evaporation.
Embodiment 2：
By furancarboxylic acid（100g,0.526mol）Add ethanol (600mL) simultaneously to stir, be heated to 60 DEG C and be back to be completely dissolved, be added dropwise
Thionyl chloride (156.58g, 1.316mol), drips off for 3.5 hours, continues to flow back 5 hours, and reaction terminates.Rotary evaporation is concentrated, and is returned
Receive ethanol.Remaining concentrate dilute with water, n-hexane (3 × 300mL) extraction, merge organic phase, respectively with 5% sodium carbonate liquor,
Saturated common salt water washing, anhydrous sodium sulfate drying, filtration obtain the bromo- 2- ethyl furoates sterlings of 5- after the concentration of filtrate rotary evaporation.
Embodiment 3：
By furancarboxylic acid（100g,0.526mol）Add ethanol (600mL) simultaneously to stir, be heated to 80 DEG C and be back to be completely dissolved, be added dropwise
Thionyl chloride (125.26g, 1.053mol), drips off for 3 hours, continues to flow back 6 hours, and reaction terminates.Rotary evaporation is concentrated, and is reclaimed
Ethanol.Remaining concentrate dilute with water, n-hexane (3 × 200mL) extraction, merge organic phase, respectively with 5% sodium carbonate liquor, full
And brine It, anhydrous sodium sulfate drying, filtration, obtain the bromo- 2- ethyl furoates sterlings of 5- after the concentration of filtrate rotary evaporation.
Embodiment 4
By furancarboxylic acid（100g,0.526mol）Add ethanol (600mL) simultaneously to stir, be heated to 70 DEG C and be back to be completely dissolved, be added dropwise
Thionyl chloride (93.9g, 0.789mol), drips off for 2.5 hours, continues to flow back 7 hours, and reaction terminates.Rotary evaporation is concentrated, and is reclaimed
Ethanol.Remaining concentrate dilute with water, n-hexane (3 × 100mL) extraction, merge organic phase, respectively with 5% sodium carbonate liquor, full
And brine It, anhydrous sodium sulfate drying, filtration, obtain the bromo- 2- ethyl furoates sterlings of 5- after the concentration of filtrate rotary evaporation.
Embodiment 5：
By furancarboxylic acid（100g,0.526mol）Add ethanol (600mL) simultaneously to stir, be heated to 60 DEG C and be back to be completely dissolved, be added dropwise
Thionyl chloride (93.9g, 0.789mol), drips off for 1.5 hours, continues to flow back 8 hours, and reaction terminates.Rotary evaporation is concentrated, and is reclaimed
Ethanol.Remaining concentrate dilute with water, n-hexane (3 × 100mL) extraction, merge organic phase, respectively with 5% sodium carbonate liquor, full
And brine It, anhydrous sodium sulfate drying, filtration, obtain the bromo- 2- ethyl furoates sterlings of 5- after the concentration of filtrate rotary evaporation.
Claims (4)
1. the preparation method of the bromo- 2- ethyl furoates of a kind of 5-, it is characterised in that：Comprise the following steps：By furancarboxylic acid and ethanol according to
Certain ratio is mixed and stirred for, and is heated to 60 DEG C -80 DEG C and is back to be completely dissolved, and according to certain ratio protochloride is added
Sulfone, 1-4 hours are dripped off, and continue the 5-8 hours that flow back, and reaction terminates；Rotary evaporation is concentrated, and reclaims ethanol；Remaining concentrate is added
Water dilution, n-hexane extraction, respectively with weak caustic solution and saturated common salt water washing, anhydrous sodium sulfate drying, rotary evaporation concentration
The bromo- 2- ethyl furoates sterlings of 5- are obtained afterwards.
2. the preparation method of bromo- 2 ethyl furoates of 5- according to claim 1, it is characterised in that：Ethanol be both reactant again
It is solvent.
3. the preparation method of the bromo- 2- ethyl furoates of 5- according to claim 1 and 2, it is characterised in that：Furancarboxylic acid and protochloride
The molar ratio of sulfone is：1：1.5 to 1：3.
4. the preparation method of the bromo- 2- ethyl furoates of 5- according to claim 1 and 2, it is characterised in that：Alkali is bicarbonate
One kind in sodium, sodium carbonate, saleratus, potassium carbonate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611037801.0A CN106632175A (en) | 2016-11-23 | 2016-11-23 | Preparation method of ethyl 5-bromo-2-furoate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611037801.0A CN106632175A (en) | 2016-11-23 | 2016-11-23 | Preparation method of ethyl 5-bromo-2-furoate |
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| CN106632175A true CN106632175A (en) | 2017-05-10 |
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| CN201611037801.0A Pending CN106632175A (en) | 2016-11-23 | 2016-11-23 | Preparation method of ethyl 5-bromo-2-furoate |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN87107535A (en) * | 1986-12-24 | 1988-08-31 | 阿勒根公司 | Ethynyl heteroaromatic carboxylic acids with retinoid activity |
-
2016
- 2016-11-23 CN CN201611037801.0A patent/CN106632175A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN87107535A (en) * | 1986-12-24 | 1988-08-31 | 阿勒根公司 | Ethynyl heteroaromatic carboxylic acids with retinoid activity |
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Effective date of registration: 20200507 Address after: Chenzhuang Town, Pucheng County, Weinan City, Shaanxi Province Applicant after: Shaanxi Youbang Biomedical Technology Co.,Ltd. Address before: 274100 Shandong city of Heze province Dingtao County Economic Development Zone, Fang Shan (Tianyuan West) Applicant before: SHANDONG YOUBANG BIOCHEMICAL TECHNOLOGY Co.,Ltd. |
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Application publication date: 20170510 |