CN116082131B - Method for synthesizing 1-indanone compound by one-pot method - Google Patents

Method for synthesizing 1-indanone compound by one-pot method Download PDF

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CN116082131B
CN116082131B CN202210731973.7A CN202210731973A CN116082131B CN 116082131 B CN116082131 B CN 116082131B CN 202210731973 A CN202210731973 A CN 202210731973A CN 116082131 B CN116082131 B CN 116082131B
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trifluoromethanesulfonic acid
acid
synthesizing
chloride
indanone
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CN116082131A (en
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刘辉
刘明荣
陆军
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Suzhou Huadao Biological Pharmacy Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

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Abstract

The invention discloses a method for synthesizing a 1-indanone compound by a one-pot method, which takes arene and 3-chloropropionyl chloride as raw materials, and the 1-indanone compound is generated by reaction under the action of an acidic catalyst in ionic liquid. The invention takes arene and 3-chloropropionyl chloride as raw materials, and the product is prepared by reaction under the action of an acidic catalyst in ionic liquid, the purity of the obtained product is high, the yield is stabilized to be more than 94%, the yield is ideal, the process operation is simple and convenient, the ionic liquid which is recycled can be recovered as a reaction medium, the production of organic waste liquid is reduced, the treatment cost is saved, and the process is environment-friendly.

Description

Method for synthesizing 1-indanone compound by one-pot method
Technical Field
The invention relates to the technical field of organic compound synthesis, in particular to a method for synthesizing a 1-indanone compound by a one-pot method.
Background
Indanones are an important and very useful class of compounds, and numerous natural products have been found to contain indenone building blocks, the basic structures of which include 1-indenone, 2-indenone, 1, 2-indendione, 1, 3-indendione, ninhydrin, and the like. Indanone structure widely exists in many natural products of plant and marine sources, has good biological activity, and has become an important skeleton of anti-parkinsonism rasagiline hydrochloride, antidepressant and tranquilizer drug molecules and the like. Recently, indane ring-containing compounds-ABT-102 have also been found to be effective in reducing inflammatory responses, post-operative pain, osteoarthritis and cancer pain in rodent models. In addition, multiple doses of ABT-102 for 5-12 consecutive days can further increase its analgesic activity, while the associated TPPV 1-induced hyperthermia effect gradually disappeared.
Meanwhile, research also finds that the indenone can be used as an extremely important synthetic intermediate, and is applied to the synthesis of materials such as dye, photochromism, organic luminescence and the like in fine organic chemical production. For example, star-shaped materials, tertiary butyl substituted trimeric indenes, can be prepared starting from 5-tertiary butyl-1-indanone. Therefore, research for searching for a method for synthesizing 1-indanone has been a popular field of research by academic workers such as chemistry.
The main methods for synthesizing 1-indanone at present are as follows: the polyphosphoric acid catalytic cyclization method, nazarov cyclization method, ester condensation method, intramolecular friedel-crafts cyclization method, pinacol rearrangement method, photochemical synthesis method and the like, which mostly generate a large amount of hazardous wastes such as waste water, and have the defects of environmental pollution, difficult operation, low yield and the like.
For example, chinese patent CN 105348062B discloses a preparation method of 3-aryl-1-indanone derivative. This method has the following disadvantages: 1. the reaction yield is low and unstable, and most of the reaction yield is concentrated between 45% and 70%; 2. the reaction time is long, the reaction is required to be carried out for 24 hours at 50 ℃, the energy consumption is high, and the period is long; 3. the amount of the organic waste liquid is large, and the post-treatment cost is increased.
In order to overcome the defects of the synthesis processes, the synthesis of the 1-indanone compound with the diversity meets the market demand, and the search of a novel synthesis process for preparing the 1-indanone compound has very important significance.
Disclosure of Invention
The invention solves the problems existing in the preparation process of the 1-indanone compound in the prior art by providing a method for synthesizing the 1-indanone compound by a one-pot method.
In order to solve the technical problems, the invention provides a method for synthesizing a 1-indanone compound by a one-pot method, which takes arene and 3-chloropropionyl chloride as raw materials and generates the 1-indanone compound by reaction under the action of an acidic catalyst in ionic liquid.
In a preferred embodiment of the present invention, the ratio of the amounts of the aromatic hydrocarbon, 3-chloropropionyl chloride and acidic catalyst is 1:1 to 1.2:0.05 to 0.2.
In a preferred embodiment of the present invention, the volume ratio of the ionic liquid to the raw material is 1:2-8.
In a preferred embodiment of the invention, the reaction temperature is 0-100 ℃ and the reaction time is below 4 hours.
In a preferred embodiment of the invention, the reaction temperature is between 0 and 60 ℃.
In a preferred embodiment of the present invention, the 3-chloropropionyl chloride is added dropwise to the mixed solution of the ionic liquid, the acidic catalyst and the aromatic hydrocarbon at a temperature of between 0 and 15 ℃.
In a preferred embodiment of the present invention, the ionic liquid comprises at least one of 1, 3-dimethylimidazole chloride salt, 1, 3-dimethylimidazole tetrafluoroborate, 1, 3-dimethylimidazole hexafluorophosphate, 1-ethyl-3-methylimidazole chloride salt, 1-ethyl-3-methylimidazole tetrafluoroborate, 1-ethyl-3-methylimidazole hexafluorophosphate, 1-butyl-3-methylimidazole chloride salt, 1-butyl-3-methylimidazole tetrafluoroborate, 1-butyl-3-methylimidazole hexafluorophosphate, 1-hexyl-3-methylimidazole chloride salt, 1-hexyl-3-methylimidazole tetrafluoroborate, or 1-hexyl-3-methylimidazole hexafluorophosphate.
In a preferred embodiment of the present invention, the ionic liquid comprises at least one of 1, 3-dimethylimidazole tetrafluoroborate, 1, 3-dimethylimidazole hexafluorophosphate, 1-ethyl-3-methylimidazole tetrafluoroborate, 1-ethyl-3-methylimidazole hexafluorophosphate, or 1-butyl-3-methylimidazole hexafluorophosphate.
In a preferred embodiment of the present invention, the acidic catalyst comprises at least one of hydrochloric acid, sulfuric acid, phosphoric acid, perchloric acid, trifluoromethanesulfonic acid, methanesulfonic acid, aluminum trichloride, zinc chloride, ferric chloride, stannic chloride, aluminum triflate, sodium triflate, lithium triflate, copper triflate, indium triflate, silver triflate, zinc triflate, magnesium triflate, scandium triflate, tin triflate, nickel triflate, or lanthanum triflate.
In a preferred embodiment of the present invention, the acidic catalyst comprises at least one of sulfuric acid, trifluoromethanesulfonic acid, aluminum trichloride, copper trifluoromethanesulfonic acid, indium trifluoromethanesulfonic acid, or scandium trifluoromethanesulfonic acid.
The beneficial effects of the invention are as follows: according to the method for synthesizing the 1-indanone compound by the one-pot method, aromatic hydrocarbon and 3-chloropropionyl chloride are used as raw materials, under the action of an acidic catalyst in the ionic liquid, the purity of the obtained product is high, the yield is stable to be over 94%, the yield is ideal, the process operation is simple and convenient, the ionic liquid which is recycled can be recycled as a reaction medium, the production of organic waste liquid is reduced, the treatment cost is saved, and the process is environment-friendly.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of 5-tert-butyl-1-indanone prepared in example 1 of the present invention.
Detailed Description
The preferred embodiments of the present invention will be described in detail below with reference to the accompanying drawings so that the advantages and features of the present invention can be more easily understood by those skilled in the art, thereby making clear and defining the scope of the present invention.
The invention discloses a method for synthesizing a 1-indanone compound by a one-pot method. The method takes arene and 3-chloropropionyl chloride as raw materials, and the 1-indanone compound is generated by reaction at 0-100 ℃ under the action of an acidic catalyst in ionic liquid. The obtained reaction product is subjected to organic phase extraction, drying and column chromatography purification, and the yield of the target product 1-indanone compound is stabilized to be more than 94%.
The method utilizes the solubility difference of the product, the ionic liquid and the catalyst in water, and is convenient for effectively separating the product, so that the yield and purity of the target product 1-indanone compound are high, the reaction is completed by a one-pot method, the process operation is simple and convenient, and the implementation and the industrial production are easy.
In addition, the ionic liquid is used as a reaction medium, so that the ionic liquid is not only beneficial to the effective synthesis, separation and purification of products, but also can be recycled, the production waste liquid is reduced, the treatment cost is saved, and the process is environment-friendly.
Specifically, the ratio of the amounts of the aromatic hydrocarbon, 3-chloropropionyl chloride and the acidic catalyst is 1:1 to 1.2:0.05 to 0.2; the volume ratio of the ionic liquid to the raw materials (aromatic hydrocarbon and 3-chloropropionyl chloride) is 1:2-8.
The reaction temperature is preferably 0-60 ℃, the reaction time is less than 4 hours, the production period is short, and the efficiency is high; and the ionic liquid, the acid catalyst and the aromatic hydrocarbon are firstly mixed, the temperature of the mixed solution is controlled to be between 0 and 15 ℃, and then 3-chloropropionyl chloride is slowly added dropwise into the mixed system at the temperature for reaction. Because the reaction activity of the reaction is generally higher, the production of isomers is reduced and the yield and purity of the target product are improved by controlling the temperature of the reaction system and the dropping speed of the acyl chloride.
The ionic liquid comprises at least one of 1, 3-dimethyl imidazole chloride salt, 1, 3-dimethyl imidazole tetrafluoroborate, 1, 3-dimethyl imidazole hexafluorophosphate, 1-ethyl-3-methyl imidazole chloride salt, 1-ethyl-3-methyl imidazole tetrafluoroborate, 1-ethyl-3-methyl imidazole hexafluorophosphate, 1-butyl-3-methyl imidazole chloride salt, 1-butyl-3-methyl imidazole tetrafluoroborate, 1-butyl-3-methyl imidazole hexafluorophosphate, 1-hexyl-3-methyl imidazole chloride salt, 1-hexyl-3-methyl imidazole tetrafluoroborate or 1-hexyl-3-methyl imidazole hexafluorophosphate.
The acidic catalyst comprises at least one of hydrochloric acid, sulfuric acid, phosphoric acid, perchloric acid, trifluoromethanesulfonic acid, methanesulfonic acid, aluminum trichloride, zinc chloride, ferric chloride, tin chloride, aluminum trifluoromethanesulfonic acid, sodium trifluoromethanesulfonic acid, lithium trifluoromethanesulfonic acid, copper trifluoromethanesulfonic acid, indium trifluoromethanesulfonic acid, silver trifluoromethanesulfonic acid, zinc trifluoromethanesulfonic acid, magnesium trifluoromethanesulfonic acid, scandium trifluoromethanesulfonic acid, tin trifluoromethanesulfonic acid, nickel trifluoromethanesulfonic acid or lanthanum trifluoromethanesulfonic acid.
The reaction process or mechanism of the invention is as follows:
example 1
Synthesis of 5-tert-butyl-1-indanone
To the reaction flask, 20 ml of 1, 3-dimethylimidazole chloride salt and 1 g of sulfuric acid were added, followed by stirring for 30 minutes, and then 13.4 g of t-butylbenzene were added, followed by stirring for 10 minutes, to obtain a mixed system. And cooling the reaction bottle by adopting ice water, controlling the temperature of a mixed system in the reaction bottle to be 10 ℃, slowly dropwise adding 14 g of 3-chloropropionyl chloride, stirring for 1 hour at the temperature of 10 ℃ after the dropwise adding is finished, and finally heating to the temperature of 45 ℃ and stirring for 2 hours.
The reaction formula is:
the reaction flask was cooled to room temperature, diluted with 100 ml of water, extracted 3 times with petroleum ether, the organic phases were combined, washed 2 times with water, dried over anhydrous sodium sulfate, filtered, concentrated to remove the organic solvent, and the remainder was purified by flash column chromatography with petroleum ether as eluent: ethyl acetate=20:1 (v/v), removal of solvent gave 18.1 g of product in 96% yield and 99.6% gas phase purity.
The structure of 5-tertiary butyl-1-indanone is identified, and the nuclear magnetic data are as follows:
1H NMR (400 MHz, CDCl 3) 1.36 (s, 9H), 2.67-2.69 (m, 2H), 3.11-3.14 (m, 2H), 7.42 (d, J=8 Hz, 1H), 7.49 (s, 1H), 7.70 (d, J=8 Hz, 1H). The nuclear magnetic spectrum is shown in figure 1.
Analysis results show that the obtained target product is correct.
Example 2
Synthesis of 5-methyl-1-indanone
To the reaction flask, 20 ml of 1, 3-dimethylimidazole chloride salt and 0.7 g of aluminum trichloride were added, followed by stirring for 30 minutes, 9.2 g of toluene was further added, and stirring was performed for 10 minutes, to obtain a mixed system. Cooling the reaction bottle by adopting ice salt, controlling the temperature of a mixed system in the reaction bottle to be 0 ℃, and then slowly dropwise adding 15 g of 3-chloropropionyl chloride; after the completion of the dropwise addition, stirring was carried out at 0℃for 1 hour, and then stirring was carried out at 40℃for 2 hours.
The reaction formula is:
the reaction flask was cooled to room temperature, diluted with 100 ml of water, extracted 3 times with petroleum ether, the organic phases were combined, washed 2 times with water, dried over anhydrous sodium sulfate, filtered, concentrated to remove the organic solvent, and the remainder was purified by flash column chromatography with petroleum ether as eluent: ethyl acetate=20:1 (v/v), removal of solvent gave 14.3 g of product in 98% yield and 99.8% gas phase purity.
The structure of 5-methyl-1-indanone is identified, and the nuclear magnetic data are:
1H NMR(400MHz,CDCl3):2.45(s,3H),2.66-2.71(m,2H),3.09-3.12(m,2H),7.18(d,J＝8.2Hz,1H),7.29(s,1H),7.68(d,J＝8.1Hz,1H)。
analysis results show that the obtained target product is correct.
Example 3
Synthesis of 1-indanone
30 ml of 1, 3-dimethylimidazole tetrafluoroborate and 2 g of copper triflate were added to the reaction flask, stirred for 30 minutes, 7.8 g of benzene was further added, and stirred for 10 minutes to obtain a mixed system. Cooling the reaction bottle by adopting ice salt, controlling the temperature of a mixed system in the reaction bottle to be 0 ℃, and slowly dropwise adding 15 g of 3-chloropropionyl chloride; after the completion of the dropwise addition, stirring was carried out at 0℃for 2 hours, and then stirring was carried out at 50℃for 1 hour.
The reaction formula is:
the reaction flask was cooled to room temperature, diluted with 100 ml of water, extracted 3 times with petroleum ether, the organic phases were combined, washed 2 times with water, dried over anhydrous sodium sulfate, filtered, concentrated to remove the organic solvent, and the remainder was purified by flash column chromatography with petroleum ether as eluent: ethyl acetate=20:1 (v/v), removal of solvent gave 12.5 g of product in 95% yield with 99.2% gas phase purity.
Identifying the structure of 1-indanone, and the nuclear magnetic data are as follows:
1H NMR(400MHz,CDCl3):2.67-2.71(m,2H),3.12-3.16(m,2H),7.34-7.39(m,1H),7.46(d,J＝7.8Hz,1H),7.55-7.61(m,1H),7.75(d,J＝7.8Hz,1H)。
analysis results show that the obtained target product is correct.
Example 4
Synthesis of 5-ethyl-1-indanone
To the reaction flask, 30 ml of 1-ethyl-3-methylimidazole hexafluorophosphate and 2.8 g of indium triflate were added, followed by stirring for 30 minutes, 10.6 g of ethylbenzene was added, and stirring for 10 minutes, to obtain a mixed system. Cooling the reaction bottle by adopting ice salt, controlling the temperature of a mixed system in the reaction bottle to be 0 ℃, and slowly dropwise adding 15 g of 3-chloropropionyl chloride; after the completion of the dropwise addition, stirring was carried out at 0℃for 2 hours, and then stirring was carried out at 45℃for 1 hour.
The reaction formula is:
the reaction flask was cooled to room temperature, diluted with 100 ml of water, extracted 3 times with petroleum ether, the organic phases were combined, washed 2 times with water, dried over anhydrous sodium sulfate, filtered, concentrated to remove the organic solvent, and the remainder was purified by flash column chromatography with petroleum ether as eluent: ethyl acetate=30:1 (v/v), removal of solvent gave 15.4 g of product in 96% yield and 99.8% gas phase purity.
The structure of 5-ethyl-1-indanone is identified, and the nuclear magnetic data are:
1H NMR(400MHz,CDCl3):1.28(t,J＝7.5Hz,3H),2.67-2.69(m,2H),2.74(q,J＝7.5Hz,2H),3.11-3.14(m,2H),7.20(m,1H),7.32(s,1H),7.69(d,J＝8Hz,1H)。
analysis results show that the obtained target product is correct.
Example 5
Synthesis of 5-chloro-1-indanone
20 ml of 1-butyl-3-methylimidazole hexafluorophosphate and 2 g of trifluoromethanesulfonic acid were added to the reaction flask, followed by stirring for 30 minutes, and 11.3 g of chlorobenzene was further added and stirring was continued for 10 minutes, to obtain a mixed system. Cooling the reaction bottle by adopting ice water, controlling the temperature of a mixed system in the reaction bottle to be 15 ℃, and slowly dropwise adding 15 g of 3-chloropropionyl chloride; after the completion of the dropwise addition, stirring was carried out at 15℃for 1 hour, and then stirring was carried out at 60℃for 1 hour while heating.
The reaction formula is:
the reaction flask was cooled to room temperature, diluted with 100 ml of water, extracted 3 times with petroleum ether, the organic phases were combined, washed 2 times with water, dried over anhydrous sodium sulfate, filtered, concentrated to remove the organic solvent, and the remainder was purified by flash column chromatography with petroleum ether as eluent: ethyl acetate=15:1 (v/v), removal of solvent gave 15.7 g of product in 94% yield with 99.5% gas phase purity.
The structure of 5-chloro-1-indanone is identified, and the nuclear magnetic data are:
1H NMR(400MHz,CDCl3):2.69-2.72(m,2H),3.12-3.15(m,2H),7.34(d,J＝8.1Hz,1H),7.48(s,1H),7.70(d,J＝8.1Hz,1H)。
analysis results show that the obtained target product is correct.
Example 6
Synthesis of 5-methoxy-1-indanone
30 ml of 1-ethyl-3-methylimidazole tetrafluoroborate and 4 g of scandium triflate were added to the reaction flask, followed by stirring for 30 minutes, 10.8 g of anisole was added, and stirring for 10 minutes, to obtain a mixed system. Cooling the reaction bottle by adopting ice water, controlling the temperature of the mixed system to be 5 ℃, and slowly dropwise adding 14 g of 3-chloropropionyl chloride; after the completion of the dropwise addition, stirring was carried out at 5℃for 1 hour, and then stirring was carried out at 40℃for 2 hours.
The reaction process is as follows:
the reaction flask was cooled to room temperature, diluted with 100 ml of water, extracted 3 times with petroleum ether, the organic phases were combined, washed 2 times with water, dried over anhydrous sodium sulfate, filtered, concentrated to remove the organic solvent, and the remainder was purified by flash column chromatography with petroleum ether as eluent: ethyl acetate=15:1 (v/v), removal of solvent gave 15.9 g of product in 98% yield and 99.6% gas phase purity.
The structure of 5-methoxy-1-indanone is identified, and the nuclear magnetic data are:
1H NMR(400MHz,CDCl3):2.68(t，J＝6Hz，2H)，3.10(t，J＝6Hz，2H)，3.88(s，3H)，6.89-6.92(m，2H),7.70(d，J＝7.5Hz，1H)。
analysis results show that the obtained target product is correct.
The foregoing description is only illustrative of the present invention and is not intended to limit the scope of the invention, and all equivalent structures or equivalent processes or direct or indirect application in other related technical fields are included in the scope of the present invention.

Claims (8)

1. A method for synthesizing 1-indanone compound by a one-pot method is characterized in that aromatic hydrocarbon and 3-chloropropionyl chloride are used as raw materials, and the 1-indanone compound is generated by reaction under the action of an acidic catalyst in ionic liquid; the ionic liquid is at least one of 1, 3-dimethyl imidazole chloride salt, 1, 3-dimethyl imidazole tetrafluoroborate, 1, 3-dimethyl imidazole hexafluorophosphate, 1-ethyl-3-methyl imidazole chloride salt, 1-ethyl-3-methyl imidazole tetrafluoroborate, 1-ethyl-3-methyl imidazole hexafluorophosphate, 1-butyl-3-methyl imidazole chloride salt, 1-butyl-3-methyl imidazole tetrafluoroborate, 1-butyl-3-methyl imidazole hexafluorophosphate, 1-hexyl-3-methyl imidazole chloride salt, 1-hexyl-3-methyl imidazole tetrafluoroborate or 1-hexyl-3-methyl imidazole hexafluorophosphate; the acid catalyst is at least one of hydrochloric acid, sulfuric acid, phosphoric acid, perchloric acid, trifluoromethanesulfonic acid, methanesulfonic acid, aluminum trichloride, zinc chloride, ferric chloride, stannic chloride, aluminum trifluoromethanesulfonic acid, sodium trifluoromethanesulfonic acid, lithium trifluoromethanesulfonic acid, copper trifluoromethanesulfonic acid, indium trifluoromethanesulfonic acid, silver trifluoromethanesulfonic acid, zinc trifluoromethanesulfonic acid, magnesium trifluoromethanesulfonic acid, scandium trifluoromethanesulfonic acid, tin trifluoromethanesulfonic acid, nickel trifluoromethanesulfonic acid or lanthanum trifluoromethanesulfonic acid.
2. The method for synthesizing 1-indanone compound according to claim 1, wherein the ratio of the amounts of the aromatic hydrocarbon, 3-chloropropionyl chloride and acidic catalyst is 1:1 to 1.2:0.05 to 0.2.
3. The method for synthesizing 1-indanone compound according to claim 2, wherein the volume ratio of the ionic liquid to the raw material is 1:2-8.
4. The method for synthesizing a 1-indanone compound according to claim 3, wherein the reaction temperature is 0 to 100 ℃ and the reaction time is 4 hours or less.
5. The method for synthesizing 1-indanone compound according to claim 4, wherein the reaction temperature is 0-60 ℃.
6. The method for synthesizing 1-indanone compound according to claim 5, wherein the 3-chloropropionyl chloride is added dropwise to a mixed solution of the ionic liquid, the acidic catalyst and the aromatic hydrocarbon at a temperature of between 0 and 15 ℃.
7. The method for synthesizing 1-indanone compound according to claim 1, wherein the ionic liquid is at least one of 1, 3-dimethylimidazole tetrafluoroborate, 1, 3-dimethylimidazole hexafluorophosphate, 1-ethyl-3-methylimidazole tetrafluoroborate, 1-ethyl-3-methylimidazole hexafluorophosphate, or 1-butyl-3-methylimidazole hexafluorophosphate.
8. The method for synthesizing 1-indanone compound according to claim 1, wherein the acidic catalyst is at least one of sulfuric acid, trifluoromethanesulfonic acid, aluminum trichloride, copper trifluoromethanesulfonate, indium trifluoromethanesulfonate, or scandium trifluoromethanesulfonate.
CN202210731973.7A 2022-06-26 2022-06-26 Method for synthesizing 1-indanone compound by one-pot method Active CN116082131B (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110207714A1 (en) * 2008-10-30 2011-08-25 Carruthers Nicholas I Serotonin receptor modulators
CN112939756A (en) * 2021-03-03 2021-06-11 上海鼎素精细化工有限公司 Improved process for preparing 5-chloro-indanone
CN113527075A (en) * 2021-07-19 2021-10-22 佳尔科生物科技南通有限公司 Preparation method for synthesizing 5-chloro-1-indanone by one-step method

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110207714A1 (en) * 2008-10-30 2011-08-25 Carruthers Nicholas I Serotonin receptor modulators
CN112939756A (en) * 2021-03-03 2021-06-11 上海鼎素精细化工有限公司 Improved process for preparing 5-chloro-indanone
CN113527075A (en) * 2021-07-19 2021-10-22 佳尔科生物科技南通有限公司 Preparation method for synthesizing 5-chloro-1-indanone by one-step method

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