CN113880739A - Synthesis method of polychlorinated diphenyl sulfide compound - Google Patents
Synthesis method of polychlorinated diphenyl sulfide compound Download PDFInfo
- Publication number
- CN113880739A CN113880739A CN202111327555.3A CN202111327555A CN113880739A CN 113880739 A CN113880739 A CN 113880739A CN 202111327555 A CN202111327555 A CN 202111327555A CN 113880739 A CN113880739 A CN 113880739A
- Authority
- CN
- China
- Prior art keywords
- diphenyl sulfide
- chloroiodobenzene
- polychlorinated diphenyl
- synthesizing
- polychlorinated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a synthesis method of a polychlorinated diphenyl sulfide compound, which comprises the following steps: adding chlorothiophenol into an organic solvent, then adding cesium carbonate, palladium tetratriphenylphosphine and chloroiodobenzene, reacting, and purifying to obtain the polychlorinated diphenyl sulfide compound. According to the synthesis method of the polychlorinated diphenyl sulfide compound, cesium carbonate and palladium tetratriphenylphosphine are used as catalysts, chlorothiophenol and chloroiodobenzene are used as substrates, and the chlorothiophenol and the chloroiodobenzene are subjected to coupling reaction under the action of the catalysts to form the C-S bonded polychlorinated diphenyl sulfide compound.
Description
Technical Field
The invention relates to the technical field of organic chemistry, in particular to a synthesis method of a polychlorinated diphenyl sulfide compound.
Background
The polychlorinated diphenyl sulfide belongs to sulfur-containing aromatic organic matters, and can be used for preventing and treating eosinophilic diseases, resisting high-temperature lubricants and manufacturing fireproof and insulating media; in addition, the tetrachloro diphenyl sulfide compound is also an insecticide with wide application prospect. At present, fewer standard samples are used in environmental analysis, and the preparation of the standard samples is not easy when polychlorinated diphenyl sulfide detection is carried out.
Uhlen broek was synthesized as early as 1962 from thiophenol sodium salt and polychlorobenzene to give a partial diphenyl sulfide derivative, but the reaction yield was low and time was long. In recent years, there have been reports of using different kinds of metal catalysts for forming C-S bonds to obtain diphenyl sulfide compounds. Wherein the catalytic reaction represented by copper is mainly metallic copper and monovalent copper (CuI, Cu)2O, etc.) as catalyst, various amines as ligand, in high polar solvent such as DMSO, DMF, etc., at 80-120 deg.C. Under the condition, Xu and the like react by taking iodobenzene and substituted thiophenol as raw materials to obtain a substituted diphenyl sulfide compound; elena and the like use iodobenzene derivatives and thiophenol as substrates to synthesize diphenyl sulfide compounds with substituent groups such as methoxy group, nitro group and the like. However, under such conditions, diphenyl disulfide may be formed, which is disadvantageous for subsequent purification treatment. In addition, nickel has been reported to be useful as a catalyst having high catalytic activity for the synthesis of diphenyl sulfide, and Zhang et al have reported (NHC)2Ni is used as a catalyst to synthesize part of diphenyl sulfide derivatives, and although the catalytic effect of nickel as the catalyst is better, the catalyst is difficult to obtain. Palladium-catalyzed formation of carbon-carbon and carbon-heterobonds has been highly successful in organic synthesis, however, less attempts have been made to synthesize sulfur-containing compounds using palladium catalysis because the sulfur element may poison the palladium catalyst.
Therefore, it is of great significance to find an effective method for synthesizing the polychlorinated diphenyl sulfide compound.
Disclosure of Invention
In view of the above, the present invention provides a method for synthesizing polychlorinated diphenyl sulfide compounds, so as to solve or at least partially solve the technical problems in the prior art.
The invention provides a synthesis method of a polychlorinated diphenyl sulfide compound, which comprises the following steps:
adding chlorothiophenol into an organic solvent, then adding cesium carbonate, palladium tetratriphenylphosphine and chloroiodobenzene, reacting, and purifying to obtain the polychlorinated diphenyl sulfide compound.
Preferably, in the synthesis method of the polychlorinated diphenyl sulfide compound, the reaction conditions are as follows: refluxing for 12-16 h at 105-115 ℃ in an inert gas environment.
Preferably, the purification method of the polychlorinated diphenyl sulfide compound specifically comprises the following steps: diluting and washing a product after reaction by using water, extracting a washed water phase by using petroleum ether, drying the extracted petroleum ether by using anhydrous magnesium sulfate, filtering and concentrating to obtain a crude product;
and (3) purifying the obtained crude product by using petroleum ether as an eluent through silica gel column chromatography, and then recrystallizing to finish the purification.
Preferably, in the synthesis method of the polychlorinated diphenyl sulfide compound, the organic solvent comprises toluene.
Preferably, in the synthesis method of the polychlorinated diphenyl sulfide compound, the solvent used for recrystallization comprises a mixture of n-hexane and dichloromethane.
Preferably, in the synthesis method of the polychlorinated diphenyl sulfide compound, the volume ratio of the n-hexane to the dichloromethane is (2-4): 1.
Preferably, in the synthesis method of the polychlorinated diphenyl sulfide compound, the molar volume ratio of the chlorothiophenol, the cesium carbonate, the palladium tetratriphenylphosphine, the chloroiodobenzene and the organic solvent is (0.8-1.2) mmol, (2-3) mmol, (0.05-0.15) mmol, (0.8-1.2) mmol, (8-12) mL.
Preferably, in the method for synthesizing polychlorinated diphenyl sulfide compounds, the chlorothiophenol includes any one of 3-chlorothiophenol, 2, 5-dichlorothiophenol, and 2,3,4,5, 6-pentachlorothiophenol;
the chloroiodobenzene comprises any one of 4-chloroiodobenzene, 2, 3-dichloroiodobenzene, 3-chloroiodobenzene and 3, 4-chloroiodobenzene.
Compared with the prior art, the synthesis method and the application of the polychlorinated diphenyl sulfide compound have the following beneficial effects:
(1) according to the synthesis method of the polychlorinated diphenyl sulfide compound, cesium carbonate and palladium tetratriphenylphosphine are used as catalysts, chlorothiophenol and chloroiodobenzene are used as substrates, and the chlorothiophenol and the chloroiodobenzene are subjected to coupling reaction under the action of the catalysts to form the C-S bonded polychlorinated diphenyl sulfide compound.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below. It is obvious that the drawings in the following description are only some embodiments of the invention, and that for a person skilled in the art, other drawings can be derived from them without inventive effort.
FIG. 1 is a mass spectrum of 3,4' -dichlorodiphenyl sulfide synthesized in example 1 of the present invention;
FIG. 2 is a mass spectrum of 2,5,4' -trichlorodiphenyl sulfide synthesized in example 2 of the present invention;
FIG. 3 is a mass spectrum of 2,3,2',3' -tetrachlorodiphenyl sulfide synthesized in example 3 of the present invention;
FIG. 4 is a mass spectrum of 2,3,4,5,6,3' -hexachlorodiphenyl sulfide synthesized in example 4 of this invention;
FIG. 5 is a mass spectrum of 2,3,4,5,6,3',4' -heptachlorodiphenyl sulfide synthesized in example 5 of the present invention.
Detailed Description
In the following, the technical solutions in the embodiments of the present invention will be clearly and completely described in conjunction with the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
The embodiment of the application provides a synthesis method of a polychlorinated diphenyl sulfide compound, which comprises the following steps:
adding chlorothiophenol into an organic solvent, then adding cesium carbonate, palladium tetratriphenylphosphine and chloroiodobenzene, reacting, and purifying to obtain the polychlorinated diphenyl sulfide compound.
The synthesis method of the polychlorinated diphenyl sulfide compound comprises the steps of taking cesium carbonate and tetratriphenylphosphine palladium as catalysts, taking chlorothiophenol and chloroiodobenzene as substrates, and forming a C-S bonding compound through a coupling reaction of the chlorothiophenol and the chloroiodobenzene under the action of the catalysts. The reaction route is simple to operate, the reaction liquid is easy to post-treat, the yield is good, and the method is a good new method for synthesizing the polychlorinated diphenyl sulfide compounds; the copper catalyst cannot be used because disulfide bond compounds such as-C-S-C-are produced; palladium chloride is used as a catalyst, the effect is poor, and the reaction yield is lower than 20%.
In some embodiments, the conditions of the reaction are: refluxing for 12-16 h at 105-115 ℃ in an inert gas environment.
Specifically, the inert gas may be a rare gas such as nitrogen or argon.
In some embodiments, the purification is specifically: diluting and washing a product after reaction by using water, extracting a washed water phase by using petroleum ether, drying the extracted petroleum ether by using anhydrous magnesium sulfate, filtering and concentrating to obtain a crude product;
and (3) purifying the obtained crude product by using petroleum ether as an eluent through silica gel column chromatography, and then recrystallizing to finish the purification.
Specifically, the purification is as follows: diluting and washing a product after reaction by using 90-110 mL of water, extracting a washed water phase for 3-4 times by using 15-25 mL of petroleum ether, combining extracted petroleum ether, drying by using anhydrous magnesium sulfate, filtering and concentrating to obtain a crude product;
and (3) purifying the obtained crude product by using petroleum ether as an eluent through a 300-400-mesh silica gel column chromatography, and then recrystallizing to complete the purification.
In some embodiments, the organic solvent comprises toluene, benzene, and the like.
In some embodiments, the solvent used for recrystallization comprises a mixture of n-hexane and dichloromethane.
In some embodiments, the volume ratio of n-hexane to dichloromethane is (2-4): 1.
In some embodiments, the molar volume ratio of the chlorothiophenol, cesium carbonate, palladium tetratriphenylphosphine, iodobenzene chloride and the organic solvent is (0.8-1.2) mmol, (2-3) mmol, (0.05-0.15) mmol, (0.8-1.2) mmol, (8-12) mL.
In some embodiments, the chlorothiophenol comprises any of 3-chlorothiophenol, 2, 5-dichlorothiophenol, 2,3,4,5, 6-pentachlorothiophenol;
the chloroiodobenzene includes any one of 4-chloroiodobenzene, 2, 3-dichloroiodobenzene, 3-chloroiodobenzene and 3, 4-chloroiodobenzene.
Specifically, the reaction formula of the synthesis method of the polychlorinated diphenyl sulfide compound is shown as follows:
the following further describes the synthesis method of the polychlorinated diphenyl sulfide compounds of the present application with specific examples.
Example 1
A synthesis method of polychlorinated diphenyl sulfide compounds comprises the following steps:
s1, adding 1mmol of 3-chlorothiophenol into 10mL of toluene, then adding 1mmol of 4-chloroiodobenzene, 2.5mmol of cesium carbonate and 0.1mmol of tetratriphenylphosphine palladium, refluxing for 14h at 110 ℃ in a nitrogen environment, and cooling to room temperature to obtain a reaction product;
s2, diluting and washing the reaction product in S1 by using 100mL of water, extracting the washed water phase by using 20mL of petroleum ether for 3 times, combining the extracted petroleum ether, drying the petroleum ether by using anhydrous magnesium sulfate, filtering and concentrating to obtain a crude product; and (3) purifying the obtained crude product by using petroleum ether as an eluent and using 350-mesh silica gel column chromatography, and recrystallizing the crude product by using a mixed solvent of n-hexane and dichloromethane in a volume ratio of 3:1 to obtain the 3,4' -dichlorodiphenyl sulfide.
The mass of 3,4' -dichlorodiphenyl sulfide synthesized in the above example 1 was 194mg, and the yield was 76%; the mass spectrum of the synthesized 3,4' -dichlorodiphenyl sulfide is shown in figure 1. The characterization data are as follows: a colorless liquid, and a non-coloring liquid,1H NMR(CDCl3，400MHz)δ:7.14～7.17(m,2H)，7.19～7.22(m,4H)，7.24～7.25(m,2H)；IR(KBr)ν:3052,1574,1464,1392,1256,1087,1009,867,815,769,672,490cm-1。
example 2
A synthesis method of polychlorinated diphenyl sulfide compounds comprises the following steps:
s1, adding 1mmol of 2, 5-dichlorothiophenol into 10mL of toluene, then adding 1mmol of 4-chloroiodobenzene, 2.5mmol of cesium carbonate and 0.1mmol of tetratriphenylphosphine palladium, refluxing for 14h at 110 ℃ in a nitrogen environment, and cooling to room temperature to obtain a reaction product;
s2, diluting and washing the reaction product in S1 by using 100mL of water, extracting the washed water phase by using 20mL of petroleum ether for 3 times, combining the extracted petroleum ether, drying the petroleum ether by using anhydrous magnesium sulfate, filtering and concentrating to obtain a crude product; and (3) purifying the obtained crude product by using petroleum ether as an eluent and using 350-mesh silica gel column chromatography, and recrystallizing the crude product by using a mixed solvent of n-hexane and dichloromethane in a volume ratio of 3:1 to obtain the 2,5,4' -trichlorodiphenyl sulfide.
The mass of the 2,5,4' -trichlorodiphenyl sulfide synthesized in the above example 2 was 240mg, and the yield was 83%; the mass spectrum of the synthesized 2,5,4' -trichlorodiphenyl sulfide is shown in figure 2. The characterization data are as follows: white crystals, m.p.48-50 ℃;1H NMR(CDCl3,400MHz)δ：6.84(d,J＝2.0Hz,1H)，7.08(dd,J＝2.4,8.4Hz,1H)，7.30(d,J＝8.4Hz,1H)，7.40(s,4H)；IR(KBr)ν:3437,1567,1475,1448,1214,1033,1014,820,501cm-1。
example 3
A synthesis method of polychlorinated diphenyl sulfide compounds comprises the following steps:
s1, adding 1mmol of 2, 3-dichlorothiophenol into 10mL of toluene, then adding 1mmol of 2, 3-dichloroiodobenzene, 2.5mmol of cesium carbonate and 0.1mmol of tetratriphenylphosphine palladium, refluxing for 14h at 110 ℃ in a nitrogen environment, and cooling to room temperature to obtain a reaction product;
s2, diluting and washing the reaction product in S1 by using 100mL of water, extracting the washed water phase by using 20mL of petroleum ether for 3 times, combining the extracted petroleum ether, drying the petroleum ether by using anhydrous magnesium sulfate, filtering and concentrating to obtain a crude product; and (3) purifying the obtained crude product by using petroleum ether as an eluent and using 350-mesh silica gel column chromatography, and recrystallizing the crude product by using a mixed solvent of n-hexane and dichloromethane in a volume ratio of 3:1 to obtain the 2,3,2',3' -tetrachlorodiphenyl sulfide.
The mass of 2,3,2',3' -tetrachlorodiphenyl sulfide synthesized in the above example 3 was 220mg, and the yield was 68%; the mass spectrum of the synthesized 2,3,2',3' -tetrachlorodiphenyl sulfide is shown in figure 3. The characterization data are as follows: white crystals, m.p.113-114 ℃;1H NMR(CDCl3,400MHz)δ：6.83(d,J＝8.0Hz,2H)，7.07(t,J＝8.0Hz,2H)，7.35(d,J＝8.0Hz,2H)；IR(KBr)ν：3427,1565,1433,1397,1194,1146,1039,782,705,505cm-1。
example 4
A synthesis method of polychlorinated diphenyl sulfide compounds comprises the following steps:
s1, adding 1mmol of 2,3,4,5, 6-pentachlorothiophenol into 10mL of toluene, then adding 1mmol of 3-chloroiodobenzene, 2.5mmol of cesium carbonate and 0.1mmol of tetratriphenylphosphine palladium, refluxing for 14h at 110 ℃ in a nitrogen environment, and cooling to room temperature to obtain a reaction product;
s2, diluting and washing the reaction product in S1 by using 100mL of water, extracting the washed water phase by using 20mL of petroleum ether for 3 times, combining the extracted petroleum ether, drying the petroleum ether by using anhydrous magnesium sulfate, filtering and concentrating to obtain a crude product; and (3) purifying the obtained crude product by using petroleum ether as an eluent and using 350-mesh silica gel column chromatography, and recrystallizing the crude product by using a mixed solvent of n-hexane and dichloromethane in a volume ratio of 3:1 to obtain the 2,3,4,5,6,3' -hexachlorodiphenyl sulfide.
The mass of the 2,3,4,5,6,3' -hexachlorodiphenyl sulfide synthesized in the above example 4 is 318mg, and the yield is 81%; the mass spectrum of the synthesized 2,3,4,5,6,3' -hexachlorodiphenyl sulfide is shown in FIG. 4. The characterization data are as follows: white crystals, m.p.106-109 ℃;1H NMR(CDCl3,400MHz)δ:6.99～7.03(m,1H)，7.12～7.13(m,1H)，7.17～7.20(m,2H)；IR(KBr)ν:3430,1574,1463,1405,1334,1319,774,684,677cm-1。
example 5
A synthesis method of polychlorinated diphenyl sulfide compounds comprises the following steps:
s1, adding 1mmol of 2,3,4,5, 6-pentachlorothiophenol into 10mL of toluene, then adding 1mmol of 3, 4-chloroiodobenzene, 2.5mmol of cesium carbonate and 0.1mmol of tetratriphenylphosphine palladium, refluxing for 14h at 110 ℃ in a nitrogen environment, and cooling to room temperature to obtain a reaction product;
s2, diluting and washing the reaction product in S1 by using 100mL of water, extracting the washed water phase by using 20mL of petroleum ether for 3 times, combining the extracted petroleum ether, drying the petroleum ether by using anhydrous magnesium sulfate, filtering and concentrating to obtain a crude product; and (3) purifying the obtained crude product by using petroleum ether as an eluent and using 350-mesh silica gel column chromatography, and recrystallizing the crude product by using a mixed solvent of n-hexane and dichloromethane in a volume ratio of 3:1 to obtain the 2,3,4,5,6,3',4' -heptachlorodiphenyl sulfide.
The mass of 2,3,4,5,6,3',4' -heptachlorodiphenyl sulfide synthesized in the above example 5 was 355mg, and the yield was 83%; the mass spectrum of the synthesized 2,3,4,5,6,3',4' -heptachlorodiphenyl sulfide is shown in figure 5. The characterization data are as follows: white crystals, m.p.118-120 ℃;1H NMR(CDCl3,400MHz)δ：6.97(dd,J＝2.4,8.4Hz,1H)，7.23(d,J＝2.4Hz,1H)，7.32(d,J＝8.4Hz,1H)；IR(KBr)v：3423,2921,1453,1336,1309,1089,1032,867,812,688cm-1。
the above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (8)
1. A method for synthesizing polychlorinated diphenyl sulfide compounds is characterized by comprising the following steps:
adding chlorothiophenol into an organic solvent, then adding cesium carbonate, palladium tetratriphenylphosphine and chloroiodobenzene, reacting, and purifying to obtain the polychlorinated diphenyl sulfide compound.
2. The method for synthesizing polychlorinated diphenyl sulfide compounds according to claim 1, wherein the reaction conditions are as follows: refluxing for 12-16 h at 105-115 ℃ in an inert gas environment.
3. The method for synthesizing polychlorinated diphenyl sulfide compounds according to claim 1, wherein the purification specifically comprises: diluting and washing a product after reaction by using water, extracting a washed water phase by using petroleum ether, drying the extracted petroleum ether by using anhydrous magnesium sulfate, filtering and concentrating to obtain a crude product;
and (3) purifying the obtained crude product by using petroleum ether as an eluent through silica gel column chromatography, and then recrystallizing to finish the purification.
4. The method for synthesizing polychlorinated diphenyl sulfide compounds according to claim 1, wherein the organic solvent comprises toluene.
5. The method for synthesizing polychlorinated diphenyl sulfide compounds as set forth in claim 1, wherein the solvent used for the recrystallization comprises a mixture of n-hexane and dichloromethane.
6. The method for synthesizing polychlorinated diphenyl sulfide compounds according to claim 5, wherein the volume ratio of the n-hexane to the dichloromethane is (2-4): 1.
7. The method for synthesizing polychlorinated diphenyl sulfide compounds as claimed in claim 1, wherein the molar volume ratio of the chlorothiophenol, the cesium carbonate, the tetratriphenylphosphine palladium, the chloroiodobenzene and the organic solvent is (0.8-1.2) mmol, (2-3) mmol, (0.05-0.15) mmol, (0.8-1.2) mmol, (8-12) mL.
8. The method for synthesizing polychlorinated diphenyl sulfide compounds as set forth in claim 1, wherein the chlorothiophenol includes any one of 3-chlorothiophenol, 2, 5-dichlorothiophenol, 2,3,4,5, 6-pentachlorothiophenol;
the chloroiodobenzene comprises any one of 4-chloroiodobenzene, 2, 3-dichloroiodobenzene, 3-chloroiodobenzene and 3, 4-chloroiodobenzene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111327555.3A CN113880739A (en) | 2021-11-10 | 2021-11-10 | Synthesis method of polychlorinated diphenyl sulfide compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111327555.3A CN113880739A (en) | 2021-11-10 | 2021-11-10 | Synthesis method of polychlorinated diphenyl sulfide compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113880739A true CN113880739A (en) | 2022-01-04 |
Family
ID=79017785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111327555.3A Pending CN113880739A (en) | 2021-11-10 | 2021-11-10 | Synthesis method of polychlorinated diphenyl sulfide compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113880739A (en) |
-
2021
- 2021-11-10 CN CN202111327555.3A patent/CN113880739A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| 张学胜等: "钯催化条件下形成碳硫键合成多氯代二苯硫醚", 《有机化学》, vol. 31, no. 7, pages 1109 - 1111 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110183378B (en) | Nicotinamide derivative and catalytic synthesis method thereof | |
| EP1626045A1 (en) | Processes for producing 3-substituted 2-chloro-5-fluoropyridine or salt thereof | |
| CN108863969B (en) | Synthesis method of 4-allyl-3, 5-disubstituted isoxazole | |
| US5883283A (en) | Process for the preparation of substituted 3-aminobenzonitriles | |
| CN114634482B (en) | Diazonium difluoro methylation reagent and synthetic method and application thereof | |
| CN113683559B (en) | Method for preparing heterocyclic o-iodosulfide | |
| MXPA97002787A (en) | Process for the preparation of 3-aminobenzonitrile replace | |
| CN117510296A (en) | Preparation method of bromine-containing intermediate alpha, beta-dibromophenylethane | |
| CN113880739A (en) | Synthesis method of polychlorinated diphenyl sulfide compound | |
| JP7545696B2 (en) | Pyrrolinone compounds and synthesis methods thereof | |
| JP2011515326A (en) | Method for producing sulfide compound using sulfide compound and organic sulfur-indium complex | |
| CN110590621B (en) | Method for synthesizing 1, 2-bis (arylsulfonyl) ethylene derivative by copper-catalyzed terminal alkyne | |
| CN113620848A (en) | Reaction method of thiophenol and o-diiodobenzene | |
| JP3759950B2 (en) | Method for producing oxirane, aziridine or cyclopropane | |
| CN110372718B (en) | Difluoromethane thiochromanonthiophene compound and preparation method thereof | |
| JP4582286B2 (en) | Sulfooxyalkynylthiophene compound and process for producing the same | |
| CN114085122B (en) | Method for synthesizing 1-iodo-alkyne compound | |
| CN112442005B (en) | N-sulfonyl imine coumarin derivative and preparation method thereof | |
| KR101004133B1 (en) | Process for production of an acetylenic compound | |
| CN102838639A (en) | Synthetic method of N-aryl-D-glucosamine | |
| JP7301337B2 (en) | Compound and its manufacturing method | |
| JP4750286B2 (en) | Method for producing novel biphenyl compound having reactive group | |
| KR101574719B1 (en) | C5 sulfone compound, method for preparing the same, method for preparing crocetin dinitrile using the same, and use thereof | |
| JP4287083B2 (en) | Process for producing 2- or 4-monosubstituted pyridine and process for selective production and separation of 4-monosubstituted pyridine or a salt thereof | |
| CN114380743A (en) | Method for introducing trifluoromethylthio group into nitrogen-containing compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |