CN115028521B - Synthesis method of 2, 2-dichloro-3, 3-trifluoropropanal - Google Patents
Synthesis method of 2, 2-dichloro-3, 3-trifluoropropanal Download PDFInfo
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- CN115028521B CN115028521B CN202210859045.9A CN202210859045A CN115028521B CN 115028521 B CN115028521 B CN 115028521B CN 202210859045 A CN202210859045 A CN 202210859045A CN 115028521 B CN115028521 B CN 115028521B
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- 238000001308 synthesis method Methods 0.000 title abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 10
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000003379 elimination reaction Methods 0.000 claims abstract description 8
- 238000009833 condensation Methods 0.000 claims abstract description 4
- 230000005494 condensation Effects 0.000 claims abstract description 4
- 230000008030 elimination Effects 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 238000007039 two-step reaction Methods 0.000 claims abstract 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 11
- 238000006482 condensation reaction Methods 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
- 229940045803 cuprous chloride Drugs 0.000 claims description 4
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 23
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 abstract description 14
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 239000005051 trimethylchlorosilane Substances 0.000 abstract description 7
- 239000007858 starting material Substances 0.000 abstract description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005695 dehalogenation reaction Methods 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000006385 ozonation reaction Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ABNQGNFVSFKJGI-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=C(Cl)C(Cl)=C1 ABNQGNFVSFKJGI-UHFFFAOYSA-N 0.000 description 1
- MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for synthesizing 2, 2-dichloro-3, 3-trifluoropropanal, which takes 1, 1-trifluorotrichloroethane, dimethyl sulfate, N-dimethylformamide and zinc powder as starting materials, and obtains the 2, 2-dichloro-3, 3-trifluoropropanal through condensation and elimination two-step reactions. The synthesis method has the advantages of fewer reaction steps, higher reaction yield and more than 70% of two-step yield, and is suitable for industrial mass production. The raw material dimethyl sulfate adopted by the synthesis method has the price of only about 1/10 of that of trimethylchlorosilane, so that the production cost is greatly reduced, the reaction condition is mild, and the operation is simple.
Description
Technical Field
The invention belongs to the technical field of pesticide intermediate synthesis, and particularly relates to a method for synthesizing 2, 2-dichloro-3, 3-trifluoropropanal.
Background
2, 2-dichloro-3, 3-trifluoropropionaldehyde (CAS number 82107-24-2) can undergo a closed-loop reaction to prepare 2, 3-dichloro-5-trifluoromethylpyridine, the latter is a key intermediate for synthesizing novel pesticides containing fluoropyridine, and a series of novel pesticides such as chlorfluazuron, chlorpyrifos, haloxyfop-methyl, chlorfluazuron and the like can be further synthesized, so that the method has wide market prospect.
The synthesis method of 2, 2-dichloro-3, 3-trifluoropropanal disclosed in the prior art mainly comprises the following steps:
1. methyl acrylate process.
1, 1-trifluoro trichloroethane and methyl methacrylate are used as starting materials, and 2, 2-dichloro-3, 3-trifluoro-propanal is obtained through four steps of addition, dehalogenation, ozonization and reduction [ see non-patent document 1 ].
The methyl acrylate method has more reaction steps and is not suitable for industrialized mass production; moreover, the dehalogenation reaction requires the use of expensive organic bases, resulting in high production costs.
2. A styrene process.
1, 1-trifluoro trichloroethane and styrene are used as starting materials, and 2, 2-dichloro-3, 3-trifluoro propanal is obtained through four steps of addition, dehalogenation, ozonization and reduction [ see Chinese patent document CN108929210A ].
The styrene method has more reaction steps and is not suitable for industrial mass production; and dimethyl sulfide adopted in the reduction reaction is extremely volatile, the smell is extremely bad, and the production environment is greatly influenced by slight leakage.
3. Formaldehyde process.
1, 1-trifluoro trichloroethane is taken as a starting material, firstly reacts with metal powder to obtain metal organic compound, then reacts with formaldehyde gas, then acid hydrolysis is carried out to obtain 2, 2-dichloro-3, 3-trifluoro propanol, and finally oxidation is carried out to obtain 2, 2-dichloro-3, 3-trifluoro propanal [ see Chinese patent document CN103420819A ].
The formaldehyde method has more reaction steps and is not suitable for industrial mass production; and formaldehyde gas has high toxicity and is extremely unfriendly to human body and environment.
4. Trimethylchlorosilane process.
1, 1-trifluorotrichloroethane, trimethylchlorosilane, N-dimethylformamide and zinc powder are used as starting materials, and 2, 2-dichloro-3, 3-trifluoropropanal is obtained through two steps of condensation and elimination (see U.S. patent document No. 4692536A and non-patent document No. 2).
Although the trimethylchlorosilane method has fewer reaction steps, the yield is lower, particularly the condensation reaction yield is only about 60 percent, and the method is not suitable for industrial mass production; in addition, the trimethylchlorosilane is exposed to air and can generate smoke, so that the operation difficulty is high; in addition, the price of trimethylchlorosilane is relatively high.
Non-patent document 1: "Convenient approaches to heterocycles via copper-catalysed additions of organic polyhalides to activated olefins", P Martin et al, tetrahedron, volume 41, 19, pages 4057-4078, 1985.
Non-patent document 2: "Synthesis of 3, 3-trifluoro-2, 2-dichloropropionaldehyde", yuan Jiliang et al, agricultural chemicals, vol.45, 7, pages 450-451, 455, month 7 of 2006.
Disclosure of Invention
The invention aims to solve the problems and provide a method for synthesizing 2, 2-dichloro-3, 3-trifluoropropanal, which has the advantages of fewer reaction steps, higher reaction yield and lower production cost and is suitable for industrial mass production.
The technical scheme for realizing the aim of the invention is as follows: the synthesis process of 2, 2-dichloro-3, 3-trifluoro-propanal includes the condensation and elimination of 1, 1-trifluoro-trichloroethane, dimethyl sulfate, N-dimethyl formamide and zinc powder as initial material to obtain 2, 2-dichloro-3, 3-trifluoro-propanal.
The reaction formula is as follows:
。
the molar ratio of the 1, 1-trifluoro trichloroethane to the dimethyl sulfate is 1:1-1:1.5.
The mol ratio of the 1, 1-trifluoro trichloroethane to the zinc powder is 1:1-1:1.5.
The molar ratio of the 1, 1-trifluoro trichloroethane to the N, N-dimethylformamide is 1:5-1:20, preferably 1:10-1:15.
In the condensation reaction, N, N-dimethylformamide is used as a reactant and a reaction solvent.
The condensation reaction is carried out in the presence of a copper catalyst; the copper catalyst is one or more than two of cuprous chloride, cupric chloride, cuprous bromide, cupric bromide, cuprous iodide and cupric iodide.
The copper catalyst is used in an amount of 0.1 to 5.0% by weight, preferably 0.5 to 2.0% by weight, based on the weight of the 1, 1-trifluorotrichloroethane.
The temperature of the condensation reaction is room temperature (20 to 30 ℃ C., the same applies below).
The temperature of the elimination reaction is 50-90 ℃.
The elimination reaction is carried out in the presence of concentrated sulfuric acid; the dosage of the concentrated sulfuric acid is 1 to 3 times of the molar equivalent of the condensation reaction product.
The invention has the positive effects that:
(1) The synthesis method has the advantages of fewer reaction steps, higher reaction yield and more than 70% of two-step yield, and is suitable for industrial mass production.
(2) The raw material dimethyl sulfate adopted by the synthesis method has the price of only about 1/10 of that of trimethylchlorosilane, so that the production cost is greatly reduced, the reaction condition is mild, and the operation is simple.
Detailed Description
Example 1
The synthesis method of 2, 2-dichloro-3, 3-trifluoropropanal of this example is as follows:
(1) to a 500mL four-necked flask, 56.2g (0.3 mol) of 1, 1-trifluorotrichloroethane, 37.8g (0.3 mol) of dimethyl sulfate and 241.2g (3.3 mol) of N, N-dimethylformamide were charged under nitrogen.
After stirring uniformly, 0.5g (5 mmol) of cuprous chloride was added, cooled to 5℃and 19.6g (0.3 mol) of zinc powder was added in portions, and the reaction was carried out after about 1 hour of addition was completed and the addition was completed to room temperature.
With the progress of the reaction, the zinc powder gradually disappeared, and after the reaction at room temperature for 12 hours, the reaction liquid gradually changed from a gray black suspension to a light green clear liquid, and the reaction was stopped.
The reaction solution was subjected to petroleum ether extraction (200 mL. Times.3), petroleum ether phase combination and water washing, dried over anhydrous sodium sulfate, and concentrated to give 64.8g of a yellow transparent oily intermediate, the yield was 90.0%, and the GC content was 99.0%.
(2) 53g of concentrated sulfuric acid is added into a 250ml four-mouth bottle, the temperature is raised to 70 ℃, 64.8g of the intermediate obtained in the step (1) is added dropwise, the product is distilled off while the intermediate is added dropwise, the condensed water is frozen brine with the temperature of about-10 ℃ for about 1 hour, and 54.1g of crude product is distilled off altogether.
The crude product is rectified to obtain 40.1g of colorless transparent oily product with the yield of 82.1% and the GC content of 97.7%.
The two-step yield was 73.8% based on 1, 1-trifluorotrichloroethane.
Example 2
The synthesis method of 2, 2-dichloro-3, 3-trifluoropropanal of this example is as follows:
(1) to a 500mL four-necked flask, 241.2g (3.3 mol) of N, N-dimethylformamide, 37.8g (0.3 mol) of dimethyl sulfate, 19.6g (0.3 mol) of zinc powder and 0.5g (5 mmol) of cuprous chloride were charged under nitrogen.
After stirring uniformly, the mixture was cooled to 5℃and 56.2g (0.3 mol) of 1, 1-trifluorotrichloroethane was added dropwise thereto, and the mixture was allowed to stand at room temperature after completion of the dropwise addition for about 1 hour.
With the progress of the reaction, the zinc powder gradually disappeared, and after the reaction at room temperature for 12 hours, the reaction liquid gradually changed from a gray black suspension to a light green clear liquid, and the reaction was stopped.
The reaction solution was extracted with petroleum ether (200 mL. Times.3), the petroleum ether phases were combined and washed with water, dried over anhydrous sodium sulfate, and concentrated to give 62.6g of a yellow transparent oily intermediate, yield 86.9%, and GC content 98.2%.
(2) 51.2g of concentrated sulfuric acid is added into a 250mL four-necked flask, the temperature is raised to 70 ℃, 62.6g of the intermediate obtained in the step (1) is added dropwise, the product is distilled off while the intermediate is added dropwise, the condensed water is frozen brine at the temperature of about-10 ℃ for about 1 hour, and 48.9g of crude product is distilled off altogether.
The crude product is rectified to obtain 38.2g of colorless transparent oily product with the yield of 80.9% and the GC content of 98.5%.
The yield in two steps was 70.3% based on 1, 1-trifluorotrichloroethane.
Claims (7)
1. A method for synthesizing 2, 2-dichloro-3, 3-trifluoropropanal is characterized in that: 1, 1-trifluoro trichloroethane, dimethyl sulfate, N-dimethylformamide and zinc powder are taken as initial raw materials, and 2, 2-dichloro-3, 3-trifluoro-propanal is obtained through condensation and elimination two-step reactions; the condensation reaction is carried out in the presence of a copper catalyst; the copper catalyst is one or more than two of cuprous chloride, cuprous bromide and cuprous iodide; the elimination reaction is carried out in the presence of concentrated sulfuric acid; the dosage of the concentrated sulfuric acid is 1 to 3 times of the molar equivalent of the condensation reaction product.
2. The method for synthesizing 2, 2-dichloro-3, 3-trifluoropropanal according to claim 1, wherein: the molar ratio of the 1, 1-trifluoro trichloroethane to the dimethyl sulfate is 1:1-1:1.5.
3. The method for synthesizing 2, 2-dichloro-3, 3-trifluoropropanal according to claim 1, wherein: the mol ratio of the 1, 1-trifluoro trichloroethane to the zinc powder is 1:1-1:1.5.
4. The method for synthesizing 2, 2-dichloro-3, 3-trifluoropropanal according to claim 1, wherein: the mol ratio of the 1, 1-trifluoro trichloroethane to the N, N-dimethylformamide is 1:10-1:15.
5. The method for synthesizing 2, 2-dichloro-3, 3-trifluoropropanal according to claim 4, wherein: the dosage of the copper catalyst is 0.5-2.0% of the weight of the 1, 1-trifluoro trichloroethane.
6. The method for synthesizing 2, 2-dichloro-3, 3-trifluoropropanal according to claim 1, wherein: the temperature of the condensation reaction is room temperature.
7. The method for synthesizing 2, 2-dichloro-3, 3-trifluoropropanal according to claim 1, wherein: the temperature of the elimination reaction is 50-90 ℃.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4692536A (en) * | 1985-10-21 | 1987-09-08 | Ciba-Geigy Corporation | Process for the preparation of hemiaminals, and the use thereof |
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- 2022-07-21 CN CN202210859045.9A patent/CN115028521B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4692536A (en) * | 1985-10-21 | 1987-09-08 | Ciba-Geigy Corporation | Process for the preparation of hemiaminals, and the use thereof |
Non-Patent Citations (2)
| Title |
|---|
| 41. Fluorine-Containing Organozinc Reagents A New Formylation Reaction of Fluoroalkylzinc Halides;Robert Werner Lang;HELVETICA CHIMICA ACTA;369-373 * |
| 袁其亮 ; 沈德隆 ; 卢鑫鑫 ; 谭成侠 ; 翁建全 ; .3,3,3-三氟-2,2-二氯丙醛的合成.农药.2006,(第07期),450-451,455. * |
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