CN112920093A - Synthesis of benzene sulfonate derivative - Google Patents
Synthesis of benzene sulfonate derivative Download PDFInfo
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- CN112920093A CN112920093A CN201911246250.2A CN201911246250A CN112920093A CN 112920093 A CN112920093 A CN 112920093A CN 201911246250 A CN201911246250 A CN 201911246250A CN 112920093 A CN112920093 A CN 112920093A
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- China
- Prior art keywords
- compound
- anthraquinone
- benzene sulfonate
- synthesis
- fluoro
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to synthesis of 1-hydroxy-9, 10-anthraquinone-2- (4-fluoro) -benzene sulfonate. Stirring 1, 2-dihydroxy-9, 10-anthraquinone, p-fluorobenzenesulfonyl chloride and triethylamine as acid-removing agents for 6 hours to obtain a crude product, and recrystallizing to obtain the 1-hydroxy-9, 10-anthraquinone-2- (4-fluoro) -benzene sulfonate. The target compound can emit orange light under the excitation light of 400 nm.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and relates to a synthesis method of 1-hydroxy-9, 10-anthraquinone-2- (4-fluoro) -benzene sulfonate.
Background
1-hydroxy-9, 10-anthraquinone-2- (4-fluoro) -benzene sulfonate can emit stronger orange fluorescence under the wavelength of 400nm, can be used as a potential fluorescent probe, and in addition, the substance has certain biological activity. The method has the advantages of simple operation, low cost and high yield. In recent years, scholars at home and abroad publish a plurality of methods for synthesizing analogues.
Disclosure of Invention
The invention aims to provide a novel method for synthesizing a fluorescent probe 1-hydroxy-9, 10-anthraquinone-2- (4-fluoro) -benzene sulfonate, which is simple and convenient to operate, low in cost and high in yield.
In order to realize the purpose of the invention, 1, 2-dihydroxy-9, 10-anthraquinone is used as a raw material, and 1-hydroxy-9, 10-anthraquinone-2- (4-fluoro) -benzene sulfonate is obtained by one-step synthesis, which is characterized in that the synthetic route is as follows:
compound A Compound B
Compound C
The technical scheme adopted by the invention is expressed as follows:
(1) weighing the compound A in a flask, adding dichloromethane dried by a molecular sieve, adding triethylamine, shaking to dissolve the compound A uniformly, placing the flask in an ice water bath, stirring for half an hour, slowly dripping the compound B dissolved in the dichloromethane, and reacting at normal temperature for 6 hours after dripping.
(2) After 6h, a yellow-green solid compound C can be separated out, and a crude product C is obtained after the compound C is subjected to suction filtration. Dissolving the product with dichloromethane, recrystallizing, filtering, and washing to remove raw material A and triethylamine to obtain pure product C.
The invention has the following advantages:
1. 1-hydroxy-9, 10-anthraquinone-2- (4-fluoro) -benzene sulfonate is synthesized for the first time;
2. simple operation, simple post-treatment, low cost and high yield.
Detailed Description
The following examples will help understanding of the present invention, but the following examples are only for more specifically illustrating the preferred embodiments of the present invention and are not intended to limit the technical aspects of the present invention. The technical scheme of the invention is the technical scheme capable of achieving the purpose of the invention. I.e., the temperatures and reagents used in the examples below, may be replaced with the corresponding temperatures and reagents described above.
Example 1
1. Preparation of Compound C
Equipped with a magnetic stirrer, adding 1, 2-dihydroxy-9, 10-anthraquinone (5 mmol) into a round-bottom flask, pouring 50mL of dichloromethane dried by a molecular sieve, dropwise adding 1.5mL of triethylamine, shaking to dissolve the triethylamine uniformly, placing the flask in an ice-water bath for stirring for half an hour, slowly dropwise adding p-fluorobenzenesulfonyl chloride (7.5 mmol) dissolved in 10mL of dichloromethane, adding a drying tube device, and reacting at normal temperature for 6 hours after the dropwise adding is finished.
2. Purification of Compound C
After 6 hours of reaction, a yellow-green solid compound C can be separated out, and a crude product C is obtained after the compound C is filtered by suction. Dissolving the product with dichloromethane, recrystallizing, filtering, washing off raw material A and triethylamine to obtain pure product C, and rectifying under reduced pressure in high vacuum to obtain compound C with yield of 75%. Elemental analysis found (calculated)/%: c60.31 (63.30), H2.79 (2.78), O24.11 (24.10) S8.04 (8.05) F4.75 (4.77);1H-NMR( 300MHz, DMSO) δH:12.6（w,1H），7.2-8.4（m,8H）。
Claims (2)
1. a synthetic method of 1-hydroxy-9, 10-anthraquinone-2- (4-fluoro) -benzene sulfonate is characterized in that the synthetic route is as follows:
compound A Compound B
Compound C
The product 1-hydroxy-9, 10-anthraquinone-2- (4-fluoro) -benzene sulfonate is synthesized by the steps with 1, 2-dihydroxy-9, 10-anthraquinone as raw material, and the yield is more than 75%.
2. In the synthesis of compounds A, B-C according to claim 1, dichloromethane as solvent and triethylamine as catalyst are used, and stirred at 0 ℃ for 6 h; the molar charge ratio of compound a, compound B and triethylamine was 1:1.5:18, and in the purification of compound C according to claim 1, dichloromethane was used as the recrystallization solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911246250.2A CN112920093A (en) | 2019-12-08 | 2019-12-08 | Synthesis of benzene sulfonate derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911246250.2A CN112920093A (en) | 2019-12-08 | 2019-12-08 | Synthesis of benzene sulfonate derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112920093A true CN112920093A (en) | 2021-06-08 |
Family
ID=76162104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911246250.2A Withdrawn CN112920093A (en) | 2019-12-08 | 2019-12-08 | Synthesis of benzene sulfonate derivative |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112920093A (en) |
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2019
- 2019-12-08 CN CN201911246250.2A patent/CN112920093A/en not_active Withdrawn
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Legal Events
| Date | Code | Title | Description |
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| PB01 | Publication | ||
| PB01 | Publication | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20210608 |