CN114835646A - Imidazole trifluoromethylthio reagent and synthesis application thereof - Google Patents

Imidazole trifluoromethylthio reagent and synthesis application thereof Download PDF

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CN114835646A
CN114835646A CN202210692653.5A CN202210692653A CN114835646A CN 114835646 A CN114835646 A CN 114835646A CN 202210692653 A CN202210692653 A CN 202210692653A CN 114835646 A CN114835646 A CN 114835646A
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trifluoromethylthio
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陈超
王珍瑜
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    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
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Abstract

The invention provides a novel imidazole trifluoromethylthio reagent and synthesis application thereof, which utilize the unique reactivity of the trifluoromethylthio reagent to realize the direct trifluoromethylthio reaction of various compounds. The trifluoromethylthio reagent can be used for reacting with a series of alcohols to realize deoxidation trifluoromethylthio of the alcohols, and an alkyl trifluoromethylthio ether product is obtained with high yield.

Description

Imidazole trifluoromethylthio reagent and synthesis application thereof
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a trifluoromethylthio reagent based on an imidazole skeleton and a synthesis application thereof.
Background
Trifluoromethylthio has gained increasing attention in medicine, agricultural chemistry and material chemistry. Due to its high lipophilicity (Hansch's hydrophobic parameter p 1.44) and strong electron withdrawing property (Hammett constant: sm 0.40, sp 0.50), trifluoromethylthio group may be used to modulate lipophilicity, bioavailability and metabolic stability of newly designed molecules (angelwan Chemie,2007,119,768.).
The prior art reports a number of methods for introducing trifluoromethylthio groups into organic compounds. All these methods can be divided into two categories: first class (indirect method): the modification of a functional group to a trifluoromethylthio group is usually involved in a halogen-fluorine exchange reaction which is usually carried out under severe conditions or trifluoromethylation of a sulfur-containing compound, and this reaction requires preliminary preparation of a precursor substance and often by-product formation is observed. In another class, the direct method is the introduction of a trifluoromethylthio group on a substrate using a trifluoromethylthio reagent. This process can be divided into three sub-groups, depending on the type of trifluoromethylthio reagent used in the chemical conversion: reagents of the free radical type, of the nucleophilic trifluoromethylthio type or of the electrophilic trifluoromethylthio type.
In fact, the trifluoromethylthio group is driven to a large extent by the introduction of a new reagent for electrophilic trifluoromethylthio. For example, N- (trifluoromethylthio) phthalimide, [2 (2-iodophenyl) propan-2-yl) oxy]The reagents such as the (trifluoromethyl) sulfanilamide and the trifluoromethylsulfanilamide researched by Billard open up a new mild synthetic route for the synthetic research of the trifluoromethylthio reagent. In contrast, nucleophilic trifluoromethionylation reaction has less research on the source of trifluoromethionyl, such as AgSCF 3 、CuSCF 3 And [ Me ] 4 N]SCF 3 (Synthesis,2018,50, 4765.). In addition to the expensive cost, one of the major challenges faced by these reagents is the relative instability of the free trifluoromethylthio anion, since β elimination of fluoride will displace the required nucleophilic trifluoromethylthiolation process (Chemistry-A European Journal,2018,24, 567.). Another nucleophilic trifluoromethylthio reaction strategy is to use a stable Organic reagent to release the in situ activated trifluoromethylthio anion (Organic Letters,2013,15, 5898.). With this method, the free trifluoromethylthio anion can be generated in a more controlled manner, while the electrophile of the nucleophilic substitution reaction can be generated as part of the activation process. Therefore, how to effectively introduce the trifluoromethylthio functional group into the molecule is also one of the hot spots which are much concerned by the organic fluorine chemical industry at present.
It is well known that a hydroxyl group is a group which does not easily leave, but when an alcohol is used as a substrate for the reaction, the dehydroxylnucleophilic substitution reaction of the alcohol can be achieved by activating the substrate alcohol by adding a deoxygenating agent. This is also a very efficient way to build a range of functionalized alkane substrates. In addition, the alcohol and the derivatives thereof exist in large quantities in nature and are easy to obtain, and the compounds are stable and nontoxic, so that the compounds are good raw materials with cost benefit. In recent years, several groups have separately reported deoxytrifluoromethylation on alcohols. E.g. using AgSCF 3 (Angewandte Chemistry International Edition,2015,54,897.) and Billard reagent (European Journal of Organic Chemistry,2016,2016,1955.); the deoxytrifluoromethylthio of alcohol is realized under the condition of adding excessive tetrabutylammonium iodide, and the alcohol is activated by CuSCF under the action of Lewis acid 3 Deoxytrifluoromethylthio group of alcohol was achieved (Chemistry-A European Journal,2014,20, 9867.). One major challenge faced by most of these agents is the relative instability of the free trifluoromethylthio anion. Or using a novel benzothiazole salt BT-SCF 3 Trifluoromethylthio substituted aliphatic compounds were synthesized directly from alcohols (Chemistry-A European Journal,2019,25, 7635.). However, the preparation process of the reaction is complicated, the reaction needs to be promoted by photocatalysis, and the used photocatalyst is an iridium-containing complex and is expensive, and the price of the photocatalyst reaches about 2000 yuan per gram; secondly, the byproducts generated by the reaction are not beneficial to recycling, and the whole reagent synthesis is not easy to realize industrial scale-up production.
The invention provides a novel imidazole trifluoromethylthio reagent 1, which can react with a series of alcohols 2 to realize the deoxidation trifluoromethylthio of the alcohols and obtain an alkyl trifluoromethylthio ether product 3 with high yield.
Figure BDA0003700772080000031
The method for directly introducing trifluoromethylthio into molecules by utilizing the trifluoromethylthio reagent based on the imidazole skeleton is undoubtedly convenient, rapid and efficient, and has the advantages that: 1. in the synthesis process of the imidazole trifluoromethylthio reagent 1, the preparation process is simple; 2. compared with the prior report reagent, S atoms in the imidazole trifluoromethylthio reagent completely enter the reaction product imidazolone 4, and the by-product does not contain sulfur, so that the pollution to the environment and the harm to the body of an operator caused by the sulfur atom contained in the by-product in the industrial treatment process are avoided; 3. more noteworthy, the byproduct generated by the imidazole trifluoromethylthio reagent is imidazolone 4, which is more beneficial to industrial recovery and treatment and can reduce the investment of cost; 4. the reagent has good functional group tolerance. The whole reagent has simple and efficient synthetic steps, and is favorable for further industrialized mass production. Therefore, a novel imidazole trifluoromethylthio reagent is developed, so that trifluoromethylthio is directly introduced into molecules, and the application prospect is wide.
Disclosure of Invention
The invention aims to overcome the defects of the existing trifluoromethylthio reagent, develop a novel imidazole trifluoromethylthio reagent and the synthesis application thereof, realize the direct trifluoromethylthio of some compounds by utilizing the unique reactivity of the trifluoromethylthio reagent, and the reagent compound has the advantages of convenient synthesis, easily obtained raw materials, wide application range and the like. By using the trifluoromethylthio reagent 1, a series of reactions 2 can be carried out, and the alkyl trifluoromethylthio ether product 3 can be obtained with high yield.
Figure BDA0003700772080000041
In one aspect, the present invention provides a trifluoromethylthio reagent based on imidazole skeleton, which has a structure as shown in formula 1:
Figure BDA0003700772080000042
wherein R is phenyl or benzyl.
In another aspect, the present invention provides a method for preparing a trifluoromethylthio reagent based on imidazole skeleton. In some embodiments, the following steps are included:
step one, putting trifluoromethylsulfanyl silver and N-halogenated succinimide in a reaction container isolated from air, replacing nitrogen for 2-5 times, and injecting an organic solvent to generate a precipitate in a system; the nitrogen replacement times are selected from 2 times, 3 times, 4 times or 5 times;
secondly, dissolving 1-phenylimidazole or 1-benzylimidazole in the same organic solvent in the first step, dropwise adding the solution into the product in the first step, and stirring the solution at 40-50 ℃ for 12-20 hours after the materials are added; the reaction temperature is selected from 40 deg.C, 41 deg.C, 42 deg.C, 43 deg.C, 44 deg.C, 45 deg.C, 46 deg.C, 47 deg.C, 48 deg.C, 49 deg.C, 50 deg.C; the reaction time is selected from 12, 13, 14, 15, 16, 17, 18, 19 and 20 hours;
thirdly, after the reaction is finished, passing the reaction solution through a diatomite column, concentrating an organic phase, and purifying by silica gel column chromatography;
fourthly, dissolving the light yellow solid obtained in the third step in an organic solvent, dropwise adding methyl trifluoromethanesulfonate, and heating, refluxing and stirring the reaction mixture at the temperature of 75-85 ℃ for 12-20 hours after the materials are added; the reaction temperature is selected from 75 deg.C, 76 deg.C, 77 deg.C, 78 deg.C, 79 deg.C, 80 deg.C, 81 deg.C, 82 deg.C, 83 deg.C, 84 deg.C, 85 deg.C; the reaction time is selected from 12, 13, 14, 15, 16, 17, 18, 19 and 20 hours;
fifthly, the reaction product is dried by spinning on a rotary evaporator, and the residue is separated and purified by column chromatography to obtain the final product.
In some embodiments, the N-halo succinimide is preferably N-chlorosuccinimide (NCS) or N-bromosuccinimide (NBS).
In some embodiments, the organic solvent in the first and second steps is selected from tetrahydrofuran or dichloromethane.
In some embodiments, the organic solvent in the fourth step is selected from dichloromethane.
In some embodiments, the molar ratio of trifluoromethylsulfanyl silver, N-halosuccinimide, 1-phenylimidazole, or 1-benzylimidazole is from 1.1 to 1.3:1.2 to 1.3: 1.0. The molar amount of silver trifluoromethylsulfanyl relative to the molar amount of 1-phenylimidazole or 1-benzylimidazole is selected from 1.1, 1.15, 1.2, 1.25, 1.3; the molar amount of the N-halogenated succinimide is selected from 1.2, 1.25 and 1.3.
In some embodiments, the molar ratio of trifluoromethylthio substituted 1-phenylimidazole or 1-benzylimidazole compound to methyl triflate is 1.0:1.6 to 2.0; the molar amount of methyl trifluoromethanesulfonate is selected from 1.6, 1.7, 1.8, 1.9 and 2.0 relative to the molar amount of trifluoromethylthio substituted 1-phenylimidazole or 1-benzylimidazole compound.
In another aspect, the present invention provides a use of a trifluoromethylthio reagent for the preparation of a compound of formula 3,
Figure BDA0003700772080000051
wherein R is 1 Is H, alkyl, substituted or unsubstituted phenyl; the substituent of the phenyl is selected from methyl or halogen; r 2 Selected from H, alkyl and substituted or unsubstituted aryl, the aryl is selected from phenyl or naphthyl, and the substituent of the aryl is selected from alkyl, nitro, halogen, phenyl and methoxy.
In some embodiments, R 1 Or R 2 The alkyl group in (1) is preferably C 1 -C 6 The halogen is preferably fluorine, chlorine or bromine.
In another aspect, the present invention provides a method for preparing the compound of formula 3. In some embodiments, the compound of formula 1 is reacted with the alcohol of formula 2 in one step to obtain the compound of formula 3;
Figure BDA0003700772080000061
r in the formula 1 is selected from phenyl or benzyl;
R 1 is H, alkyl, substituted or unsubstituted phenyl, and the substituent of the phenyl is selected from methyl or halogen;
R 2 selected from H, alkyl and substituted or unsubstituted aryl, the aryl is selected from phenyl or naphthyl, and the substituent of the aryl is selected from alkyl, nitro, naphthyl,Halogen, phenyl, methoxy.
In some embodiments, R 1 Or R 2 Said alkyl in (1) is preferably C 1 -C 6 The halogen is preferably fluorine, chlorine or bromine.
In some embodiments, the method of preparing the compound of formula 3 comprises the steps of: dissolving a compound shown in a formula 2 in an organic solvent under the nitrogen atmosphere, dropwise adding an alkaline substance into the organic solvent, dissolving a compound shown in a formula 1 in the organic solvent, slowly dropwise adding the compound into a solution shown in a formula 2, stirring and reacting at 25-35 ℃ for 12-20 hours, removing the organic solvent after the reaction is finished, and separating and purifying residues through column chromatography to obtain a compound shown in a formula 3; the organic solvent is preferably one or more of tetrahydrofuran, dichloromethane or acetonitrile; the reaction temperature is selected from 25 deg.C, 26 deg.C, 27 deg.C, 28 deg.C, 29 deg.C, 30 deg.C, 31 deg.C, 32 deg.C, 33 deg.C, 34 deg.C, 35 deg.C; the reaction time is selected from 12, 13, 14, 15, 16, 17, 18, 19 and 20 hours.
In some embodiments, the basic material in the process for preparing the compound of formula 3 is selected from 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU) or N, N-diisopropylethylamine.
In some embodiments, the organic solvent in the preparation method of the compound of formula 3 is preferably one or more of tetrahydrofuran, dichloromethane, or acetonitrile.
The invention has the advantages of
The invention provides a trifluoromethylthio reagent based on an imidazole skeleton, which has the following characteristics:
1. simple synthesis method, simple and easily obtained raw materials, simple and convenient reaction operation, environmental protection and the like.
2. Overcomes the defects of relative instability of free trifluoromethylthio anion and complex preparation process.
3. The trifluoromethylthio reagent can be used for reacting with a series of alcohols to obtain alkyl trifluoromethylthio ether products with high yield.
4. The common trifluoromethanesulfonyl silver reagent needs to be stored at low temperature (0-2 ℃) and is protected from light (Angewandte Chemie International Edition,2015,54,897.), while the trifluoromethanesulfonyl reagent based on the imidazole skeleton provided by the invention is a stable solid, is not sensitive to temperature, humidity and light sources, and is extremely convenient to store and use.
Drawings
FIG. 1 shows the NMR spectrum of the product of example 1 based on a trifluoromethylthio reagent containing 1-phenylimidazole.
FIG. 2 shows the NMR spectrum of the product of example 1 based on 1-phenylimidazole in the form of trifluoromethylthio group reagent.
FIG. 3 is the NMR spectrum of the product of example 1 based on 1-phenylimidazole in the form of trifluoromethylthio group.
FIG. 4 is the NMR spectrum of 4-nitrobenzyl trifluoromethylthio ether product of example 3.
FIG. 5 is the NMR spectrum of 4-nitrobenzyltrifluoromethylthio ether product of example 3.
FIG. 6 is a NMR chart of the product 1-naphthylethyl trifluoromethylthio ether prepared in example 6.
FIG. 7 is a NMR fluorine spectrum of 1-naphthylethyltrifluoromethylthio ether which is a product obtained in example 6.
Detailed Description
The following embodiments are described in detail to solve the technical problems by applying technical means to the present invention, and the implementation process of achieving the technical effects can be fully understood and implemented.
Abbreviations
Figure BDA0003700772080000081
Example 1: synthesis of imidazole skeleton trifluoromethylthio reagent 1a
Trifluoromethylthiosilver (1-1.3eq) and N-chlorosuccinimide NCS (1.2-1.3eq) were charged in a 250ml Schlenk flask, after 2-5 times of replacement of nitrogen gas, 50-70ml of tetrahydrofuran was injected, at which time it was observed that a precipitate was generated in the system, and then 1-phenylimidazole (1.0eq) was slowly added dropwise to the reaction system, and it was sealed. Reacting for 12-20 hours at 40-50 ℃. After the reaction was completed, the reaction solution was passed through a short column of celite, and the organic phase was concentrated and purified by silica gel column chromatography to obtain the product 5a as a pale yellow solid (yield 50%).
The product 5a (1.0eq) was dissolved in dry dichloromethane and methyl triflate (1.6-2.0eq) was added dropwise. The reaction mixture was heated under reflux at 75-85 ℃ for 12-20 hours, after completion of the reaction, the solvent was spin-dried, and the residue was purified by column chromatography to give the product 1a as a brown solid (yield 80%).
1 H NMR(400MHz,Chloroform-d)δ8.10(s,1H),7.78(s,1H),7.55(s,5H),4.13(s,3H). 19 F NMR(377MHz,CDCl3)δ-39.31(s,3F),-78.99(s,3F). 13 C NMR(101MHz,Chloroform-d)(101MHz,Chloroform-d)δ134.71,131.78,131.52,130.12,128.42,128.26,127.41,126.86(q,J＝314.2Hz),126.51,125.29,120.53(q,J＝319.8Hz),37.88.HR-MS(ESI)m/z:Calcd for C 11 H 10 F 3 N 2 S + 259.0511,found[M-OTf] + :259.0499.
Example 2: synthesis of imidazole skeleton trifluoromethylthio reagent 1a
Product 5a and product 1a were prepared by replacing N-chlorosuccinimide NCS in example 1 with N-bromosuccinimide NBS using the same process conditions as in example 1. The yield of product 5a was 38% and the yield of product 1a was 80%.
Example 3: 4-nitrobenzyl trifluoromethylthio ether 3a
4-nitrobenzol (1eq.) was dissolved in dichloromethane under nitrogen atmosphere, DBU (3-3.3eq.) was added dropwise thereto, and then trifluoromethylthio reagent 1a (2.0-2.3eq.) prepared in example 1 was dissolved in a small amount of dichloromethane and slowly added dropwise thereto, and the reaction mixture was stirred at 25-35 ℃ for 12-20 hours. And after the reaction is finished, the solvent is dried in a rotating way, and the residue is separated and purified by column chromatography to obtain a 4-nitrobenzyl trifluoromethylthio ether 3a product. The yield was 96%, and the obtained product was a colorless liquid.
1 H NMR(400MHz,Chloroform-d)δ8.19(d,J＝8.0Hz,2H),7.52(d,J＝7.6Hz,2H),4.17(s,2H). 19 F NMR(377MHz,CDCl 3 )δ-41.2(s,3F).HR-MS(EI)m/z:Calcd for C 8 H 6 F 3 NO 2 S 237.0071,found[M] + :237.0079.
Example 4: 4-nitrobenzyl trifluoromethylthio ether 3a
The product 3a, 3a was prepared in 85% yield using the same process conditions as example 3 using N, N-diisopropylethylamine instead of DBU in example 3.
Example 5: 4-nitrobenzyl trifluoromethylthio ether 3a
The product 3a, 3a was prepared in 65% yield using tetrahydrofuran as a reaction solvent instead of dichloromethane in example 3, and using the same process conditions as in example 3.
Example 6: 1-Naphthalenethyltrifluoromethylthio ether 3b
1-Naphthaleneethanol (1eq.) was dissolved in dichloromethane under nitrogen atmosphere, DBU (3-3.3eq.) was added dropwise thereto, and then trifluoromethylthio reagent 1a (2.0-2.3eq.) prepared in example 1 was dissolved in a small amount of dichloromethane and slowly added dropwise thereto, and the reaction mixture was stirred at 25-35 ℃ for 12-20 hours. And after the reaction is finished, the solvent is dried by spinning, and the residue is separated and purified by column chromatography to obtain the 1-naphthyl ethyl trifluoromethyl sulfide ether product. The yield was 86%, and the product was obtained as a colorless liquid.
1 H NMR(400MHz,Chloroform-d)δ7.97(d,J＝8.3Hz,1H),7.89(d,J＝7.9Hz,1H),7.78(d,J＝8.1Hz,1H),7.60–7.47(m,1H),7.45–7.40(m,1H),7.36(d,J＝6.9Hz,1H),3.47(dd,J＝9.5,6.4Hz,2H),3.25(dd,J＝9.5,6.4Hz,2H). 19 F NMR(377MHz,CDCl3)δ-40.46(s,3F).HR-MS(EI)m/z:Calcd for C 13 H 11 F 3 S 256.0534,found[M] + :256.0542.
Example 7: 1-Naphthalenethyltrifluoromethylthio ether 3b
The product 3b was prepared using the same process conditions as example 6 using N, N-diisopropylethylamine instead of DBU in example 6, with a 75% yield of 3 b.
Example 8: 1-Naphthalenethyltrifluoromethylthio ether 3b
The product 3b was prepared using tetrahydrofuran as a reaction solvent instead of dichloromethane in example 6, and the yield of 3b was 55% using the same process conditions as in example 6.
The foregoing is directed to preferred embodiments of the present invention, other and further embodiments of the invention may be devised without departing from the basic scope thereof, and the scope thereof is determined by the claims that follow. However, any simple modification, equivalent change and modification of the above embodiments according to the technical essence of the present invention are within the protection scope of the technical solution of the present invention.

Claims (11)

1. A trifluoromethylthio reagent based on an imidazole skeleton, characterized by a compound represented by the following structural formula 1:
Figure FDA0003700772070000011
wherein R is phenyl or benzyl.
2. A method for preparing a trifluoromethylthio reagent based on an imidazole skeleton according to claim 1, wherein the method comprises the following steps: comprises that
Step one, putting trifluoromethylsulfanyl silver and N-halogenated succinimide in a reaction container isolated from air, replacing nitrogen for 2-5 times, and injecting an organic solvent to generate a precipitate in a system; the N-halosuccinimide is preferably N-chlorosuccinimide (NCS) or N-bromosuccinimide (NBS);
secondly, dissolving 1-phenylimidazole or 1-benzylimidazole in the same organic solvent in the first step, dropwise adding the solution into the product in the first step, and stirring the solution at 40-50 ℃ for 12-20 hours after the materials are added;
thirdly, after the reaction is finished, passing the reaction solution through a diatomite column, concentrating an organic phase, and purifying by silica gel column chromatography;
fourthly, dissolving the light yellow solid obtained in the third step in an organic solvent, dropwise adding methyl trifluoromethanesulfonate, and heating, refluxing and stirring the reaction mixture at the temperature of 75-85 ℃ for 12-20 hours after the materials are added;
fifthly, the reaction product is dried by spinning on a rotary evaporator, and the residue is separated and purified by column chromatography to obtain the final product.
3. A process for the preparation of trifluoromethylthio reagent according to claim 2, wherein: the organic solvent in the first step and the second step is selected from tetrahydrofuran or dichloromethane.
4. A process for the preparation of trifluoromethylthio reagent according to claim 2 or 3, wherein: the organic solvent in the fourth step is selected from dichloromethane.
5. A process for the preparation of trifluoromethylthio reagent according to any of claims 2 to 4, wherein: the molar ratio of the silver trifluoromethylthio, the N-halogenated succinimide, the 1-phenylimidazole or the 1-benzylimidazole is 1.1-1.3:1.2-1.3: 1.0.
6. A process for the preparation of trifluoromethylthio reagent according to any of claims 2 to 5, wherein: the mol ratio of the trifluoromethylthio-substituted 1-phenylimidazole or 1-benzylimidazole compound to the methyl trifluoromethanesulfonate is 1.0: 1.6-2.0.
7. Use of a trifluoromethylthio reagent according to claim 1 for the preparation of a compound of formula 3, wherein
Figure FDA0003700772070000021
Wherein R is 1 Is H, alkyl, substituted or unsubstituted phenyl, the substituent of the phenyl is selected from methyl or halogen, R 2 Selected from H, alkyl and substituted or unsubstituted aryl, the aryl is selected from phenyl or naphthyl, the substituent of the aryl is selected from alkyl, nitro, halogen, phenyl and methoxy,
R 1 or R 2 The alkyl group in (1) is preferably C 1 -C 6 The halogen is preferably fluorine, chlorine or bromine.
8. A process for preparing a compound of formula 3, characterized in that: the compound of formula 1 and the alcohol of formula 2 are reacted in one step,
Figure FDA0003700772070000022
wherein R is selected from phenyl or benzyl,
R 1 is H, alkyl, substituted or unsubstituted phenyl, the substituent of the phenyl is selected from methyl or halogen,
R 2 selected from H, alkyl and substituted or unsubstituted aryl, the aryl is selected from phenyl or naphthyl, the substituent of the aryl is selected from alkyl, nitro, halogen, phenyl and methoxy,
R 1 or R 2 The alkyl group in (1) is preferably C 1 -C 6 The halogen is preferably fluorine, chlorine or bromine.
9. The method of claim 8, wherein: dissolving a compound shown in a formula 2 in an organic solvent under the nitrogen atmosphere, dropwise adding an alkaline substance into the organic solvent, dissolving a compound shown in a formula 1 in the organic solvent, slowly dropwise adding the compound into a solution shown in a formula 2, stirring and reacting at 25-35 ℃ for 12-20 hours, removing the organic solvent after the reaction is finished, and separating and purifying residues through column chromatography to obtain a compound shown in a formula 3; the organic solvent is preferably one or more of tetrahydrofuran, dichloromethane or acetonitrile.
10. The production method according to claim 8 or 9, characterized in that: the basic substance is selected from 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU), N-diisopropylethylamine.
11. The production method according to any one of claims 8 to 10, characterized in that: the organic solvent is preferably one or more of tetrahydrofuran, dichloromethane or acetonitrile.
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