Synthesis method of trifluoromethyl-substituted arylethene compound
By reacting the aryl halide with 4,4,4-trifluoro-2-butynylic acid under a copper catalyst under an inert atmosphere, the problems of rare raw materials and expensive catalysts in the prior art are solved, and trifluoro is achieved The efficient synthesis of methyl substituted arylethylene is suitable for industrial production.
Patent Information
- Application Number
- CN202411234787.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-09-04
- Publication Date
- 2024-12-13
AI Technical Summary
The existing synthesis method of trifluoromethyl-substituted arylethylene compounds has problems such as rare raw materials, low reaction yields, and expensive catalysts, and is not suitable for industrial production.
Under an inert atmosphere, the aryl halide is reacted with 4,4,4-trifluoro-2-butynylic acid, catalyst, ligand and base in a polar solvent, and the trifluoromethyl substituted aromatics are obtained by decarboxylation reaction. Basic ethylene compounds, using copper catalysts and cheap ligands, have short steps and high efficiency.
Products with high yields (greater than 70%) and high purity (≥99.0%) are produced, which are simple to operate, low cost, and are suitable for industrial applications.
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Abstract
Description
Technical Field
[0001] The invention relates to the technical field of fine chemicals, and in particular to a method for synthesizing a trifluoromethyl-substituted arylethylene compound. Background Art
[0002] Since organic fluorine-containing compounds have unique physical properties, chemical properties and physiological activities, they have chemical stability, surface activity and excellent temperature resistance, so organic fluoride compounds are widely and deeply studied and applied in the fields of medicine, pesticides and functional materials. As an important fluorine-containing functional group, trifluoromethyl is widely used in fluorination modification of compounds and has important application value in the fields of medicine, pesticides and functional materials.
[0003] Trifluoromethyl-substituted arylethylene compounds are widely used fine chemicals and key intermediates for the synthesis of veterinary drugs such as fluralaner, afoxolaner, lotilaner, sarolaner and esafoxolaner. They can also be transformed into other trifluoromethyl-containing aromatic compounds. Their synthesis methods are also the focus of academic and industrial circles.
[0004] Deficiencies of existing technology:
[0005] At present, the preparation methods of trifluoromethyl-substituted arylethylene compounds are as follows:
[0006] (1) A trifluoromethyl-substituted aromatic vinyl compound is obtained by Wittig reaction of 2,2,2-trifluoro-substituted acetophenone and methyl-substituted phosphorus ylide (Journal of the American Chemical Society, 2015, 137, 11606-11609; Tetrahedron Asymmetry, 1994, 5, 1473-1476). This reaction generally uses a strong base, but the raw material of 2,2,2-trifluoro-substituted acetophenone with a special substituent is not easy to obtain, and sometimes the reaction yield is low, with a yield of only 24% (Angewandte Chemie-International Edition, 2015, 54, 2729-2733).
[0007] Route Scheme 1
[0008]
[0009] (2) The literature (Synthesis, 2010, 11, 1883-1890; Journal of Fluorine Chemistry, 1999, 95, 167-170; Organic Letters, 2022, 24, 7461-7464) reported that phenylboronic acid was used as the starting material and 2-bromo-3,3,3-trifluoroprop-1-ene was used to obtain trifluoromethyl-substituted aromatic vinyl under transition metal catalysis. This method requires the synthesis of phenylboronic acid as the starting material. At the same time, 2-bromo-3,3,3-trifluoroprop-1-ene is a fluorine-containing gas. It needs to be carried out in a closed system, and the transition metal catalyst is expensive.
[0010] Route Scheme 2
[0011]
[0012] (3) Patent (JP2022 / 169149,2022,A) uses phenyl Grignard reagent and 2,3,3,3-tetrafluoroprop-1-ene in an autoclave with palladium as a catalyst under high temperature conditions to obtain trifluoromethyl-substituted arylethylene, with a yield of only 48%. Literature (Journal of Fluorine Chemistry, 2009, 130, 591-594) also uses phenyl Grignard reagent and 2-bromo-3,3,3-trifluoroprop-1-ene under transition metal nickel catalysis to obtain the product.
[0013] Route Scheme 3
[0014]
[0015] (4) The literature (Synlett, 2023, 35, 347-351) reported that acetophenone was used as the starting material to undergo nucleophilic addition with trifluoromethyltrimethylsilane under KF conditions, and then dehydrated under acidic conditions to obtain the target product. The trifluoromethyltrimethylsilane reagent is relatively expensive and not suitable for industrial production.
[0016] Route Scheme 4
[0017]
[0018] (5) The literature (Tetrahedron Letters, 2001, 42, 4083-4085]) reported the use of iodobenzene as a starting material and (3,3,3-trifluoroprop-1-en-2-yl)boric acid under palladium catalysis to obtain the target product. The literature (Journal of Organic Chemistry, 1991, 56, 7336-7340) used 2-bromo-3,3,3-trifluoroprop-1-ene as a fluorine source and iodobenzene under palladium catalysis, while adding silver and zinc additives to synthesize the target product. The boric acid reagent and noble metal catalyst in this method are relatively expensive and are not suitable for industrial production.
[0019] Route Scheme 5
[0020]
[0021] (6) The literature (Journal of Fluorine Chemistry, 2023, 267, 110116) reported the use of iodobenzene as a starting material and (3,3,3-trifluoroprop-1-yne) with different regioselectivities under copper catalytic conditions.
[0022] Summary of the invention
[0023] The object of the present invention is to provide a method for synthesizing trifluoromethyl-substituted arylethylene compounds to solve one or more of the above-mentioned problems in the prior art.
[0024] The present invention provides a method for synthesizing a trifluoromethyl-substituted arylethylene compound, comprising the following steps:
[0025] S1. Under an inert atmosphere, an aryl halide, 4,4,4-trifluoro-2-butynoic acid, a catalyst, a ligand, and a base are reacted in a solvent to obtain an intermediate 1;
[0026] S2. Add an inorganic base to carry out a decarboxylation reaction to obtain a trifluoromethyl-substituted arylethylene compound.
[0027] In certain embodiments, the synthetic route is as follows:
[0028]
[0029] Wherein: R1 is selected from 1 to 5 of the following substituents, and the multiple substituents may be the same substituent or different substituents. The substituents are respectively hydrogen, C1-C6 alkyl, phenolic hydroxyl, C1-C6 alkoxy, trifluoromethyl, nitro, halogen, amino, C1-C6 alkyl substituted amino, C1-C6 alkyl substituted mercapto, C1-C6 alkyl substituted sulfoxide or C1-C6 alkyl substituted sulfone.
[0030] In certain embodiments, in step S1, the solvent is a polar solvent, and the polar solvent includes any one of dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, tetrahydrofuran, dioxane, acetone, acetonitrile, ethylene glycol dimethyl ether, toluene, xylene, N,N-dimethylformamide, and N,N-dimethylacetamide.
[0031] In certain embodiments, in step S1, the catalyst comprises CuCl, CuBr, Cu(MeCN )4 Any one of PF6, CuI, CuCN, Cu2O.
[0032] In certain embodiments, in step S1, the ligand includes any one of 1,10-phenanthroline, 2,2'-bipyridine, 4,4'-dimethoxy-2,2'-bipyridine, 6,6'-dimethyl-2,2'-bipyridine, terpyridine or N-methylpyrrolidone; and the base includes any one of triethylamine, K2CO3, Cs2CO3, pyridine, DBU, and diisopropylethylamine.
[0033] In certain embodiments, in step S1, the molar ratio of the aryl halide to 4,4,4-trifluoro-2-butynoic acid is 1:1.5-3; the molar ratio of the aryl halide to the catalyst is 1:0.01-0.5; the molar ratio of the aryl halide to the ligand is 1:0.02-1; and the molar ratio of the aryl halide to the base is 1:1.0-2.0.
[0034] In certain embodiments, the reaction temperature in step S1 is -20-200°C; and the decarboxylation reaction temperature in step S2 is 50-200°C.
[0035] In certain embodiments, in step S2, the inorganic base includes any one of NaOH, KOH, LiOH, Ca(OH)2, Na2CO3, K2CO3, NaHCO3, KHCO3, and Cs2CO3.
[0036] In certain embodiments, step S2 further comprises a post-treatment step after the decarboxylation reaction, specifically: liquid separation extraction, recovery of organic solvent, and reduced pressure distillation.
[0037] Beneficial effects: The raw materials of the present invention, aryl halide, polar solvent, 4,4,4-trifluoro-2-butynoic acid, base, copper catalyst and ligand, are all industrial products, cheap and easy to obtain. In addition, the synthesis method has the advantages of short reaction steps and high production efficiency. The trifluoromethyl-substituted arylethylene obtained by the synthesis method has a high reaction yield, and a product with a purity of ≥99.0% can be obtained with a yield of more than 70%. This simple operation and low-cost process are very suitable for industrialization and can be widely promoted and used. DETAILED DESCRIPTION
[0038] The technical solutions in the embodiments of the present invention are described clearly and completely below. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.
[0039] The present invention provides the following technical solutions:
[0040] A method for synthesizing a trifluoromethyl-substituted arylethylene compound comprises the following steps:
[0041] S1. Under an inert atmosphere, an aryl halide, 4,4,4-trifluoro-2-butynoic acid, a catalyst, a ligand, and a base are reacted in a solvent to obtain an intermediate 1;
[0042] S2. Add an inorganic base to carry out a decarboxylation reaction to obtain a trifluoromethyl-substituted arylethylene compound.
[0043] Wherein: in step S1, the molar ratio of the aryl halide to 4,4,4-trifluoro-2-butynoic acid is 1:1.5-3; the molar ratio of the aryl halide to the catalyst is 1:0.01-0.5; the molar ratio of the aryl halide to the ligand is 1:0.02-1; the molar ratio of the aryl halide to the base is 1:1.0-2.0.
[0044] The synthetic route is as follows:
[0045]
[0046] In step S1, the solvent is a polar solvent, and the polar solvent includes any one of dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, tetrahydrofuran, dioxane, acetone, acetonitrile, ethylene glycol dimethyl ether, toluene, xylene, N,N-dimethylformamide, and N,N-dimethylacetamide.
[0047] In step S1, the catalyst includes CuCl, CuBr, Cu(MeCN )4Any one of PF6, CuI, CuCN, Cu2O.
[0048] In step S1, the ligand includes any one of 1,10-phenanthroline, 2,2'-bipyridine, 4,4'-dimethoxy-2,2'-bipyridine, 6,6'-dimethyl-2,2'-bipyridine, terpyridine or N-methylpyrrolidone; the base includes any one of triethylamine, K2CO3, Cs2CO3, pyridine, DBU, and diisopropylethylamine.
[0049] Example 1
[0050] In an inert atmosphere, iodobenzene (2.04 g, 0.01 mol), 4,4,4-trifluoro-2-butynoic acid (2.07 g, 0.015 mol), CuI (0.19 g, 0.001 mol), 1,10-phenanthroline (0.36 g, 0.002 mol), K2CO3 (2.76 g, 0.02 mol) and 1,2-dichloroethane (50 mL) were added to a stirred 250 mL stainless steel reactor. The temperature was raised to 80°C for reaction for 24 hours. After the reaction was completed, the mixture was cooled to room temperature and an aqueous solution (50 mL) of NaOH (4.0 g, 0.1 mol) was heated to reflux for reaction for 12 hours. After the reaction was completed by TLC detection, an organic solvent of dichloromethane (50 mL) was added for separation. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was recovered by vacuum distillation. The crude product was subjected to vacuum distillation to obtain pure (3,3,3-trifluoroprop-1-en-2-yl)benzene (1.30 g, yield 75.6%, purity 99.1%). 1 H NMR (400MHz, CDCl3) δ7.50-7.45(m,2H),7.42-7.38(m,3H),5.97(q,J=1.3Hz,1H),5.78(q,J=1.6Hz,1H).
[0051] Example 2
[0052] In an inert atmosphere, 4-methyliodobenzene (2.18 g, 0.01 mol), 4,4,4-trifluoro-2-butynoic acid (2.72 g, 0.02 mol), CuBr (0.14 g, 0.001 mol), 2,2'-bipyridine (0.31 g, 0.002 mol), Cs2CO3 (3.26 g, 0.01 mol) and chloroform (50 mL) were added to a stirred 250 mL stainless steel reactor. The temperature was raised to 80°C for reaction for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, and an aqueous solution (50 mL) of KOH (5.6 g, 0.1 mol) was added. The mixture was heated to reflux for reaction for 12 hours. After the reaction was completed by TLC detection, an organic solvent, dichloromethane (50 mL), was added for separation. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was recovered by vacuum distillation. The crude product was subjected to vacuum distillation to obtain pure 1-methyl-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene (1.45 g, yield 78.0%, purity 99.0%).
[0053] 1 H NMR (400MHz, CDCl3): δ7.37(d,J=8.1Hz,2H), 7.21(d,J=7.9Hz,2H), 5.92(q,J=1.4Hz,1H), 5.75(q,J=1.7Hz,1H), 2.39(s,3H).
[0054] Example 3
[0055] In an inert atmosphere, 4-methoxyiodobenzene (2.34 g, 0.01 mol), 4,4,4-trifluoro-2-butynoic acid (4.14 g, 0.03 mol), Cu(MeCN)4PF6 (0.372 g, 0.001 mol), 4,4'-dimethoxy-2,2'-bipyridine (0.43 g, 0.002 mol), DBU (1.52 g, 0.01 mol) and dioxane (50 mL) were added to a stirred 250 mL stainless steel reactor. The temperature was raised to 100°C for reaction for 18 hours. After the reaction was completed, the mixture was cooled to room temperature, an aqueous solution (50 mL) of LiOH (2.4 g, 0.1 mol) was added, and the mixture was heated to reflux for reaction for 24 hours. After the reaction was completed by TLC detection, an organic solvent EA (50 mL) was added for separation. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was recovered by vacuum distillation. The crude product was subjected to vacuum distillation to obtain pure 1-methoxy-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene (1.71 g, yield 84.6%, purity 99.5%).
[0056] 1H NMR (400MHz, CDCl3): δppm 7.40 (d, J = 8.5Hz, 2H), 6.93-6.90 (m, 2H), 5.87 (q, J = 1.3Hz, 1H), 5.70 (q, J = 1.7Hz, 1H), 3.83 (s, 3H).
[0057] Example 4
[0058] In an inert atmosphere, 4-trifluoromethyliodobenzene (2.72 g, 0.01 mol), 4,4,4-trifluoro-2-butynoic acid (2.72 g, 0.02 mol), CuI (0.19 g, 0.001 mol), 2,2'-bipyridine (0.31 g, 0.002 mol), Cs2CO3 (3.26 g, 0.01 mol) and toluene (50 mL) were added to a stirred 250 mL stainless steel reactor. The temperature was raised to 120°C for reaction for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and an aqueous solution (50 mL) of KOH (5.6 g, 0.1 mol) was added. The mixture was heated to reflux for reaction for 12 hours. After the reaction was completed by TLC detection, an organic solvent, ethyl acetate (50 mL), was added for separation. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was recovered by vacuum distillation. The crude product was subjected to vacuum distillation to obtain pure 1-(trifluoromethyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene (2.02 g, yield 84.2%, purity 99.3%). 1 H NMR (400MHz, CDCl3): δ7.64 (d, J = 8.2 Hz, 2H), 7.56 (d, J = 8.1 Hz, 2H), 6.05 (d, J = 1.5 Hz, 1H), 5.83 (d, J = 1.9 Hz, 1H).
[0059] Example 5
[0060] In an inert atmosphere, 4-nitroiodobenzene (2.49 g, 0.01 mol), 4,4,4-trifluoro-2-butynoic acid (2.72 g, 0.02 mol), CuI (0.95 g, 0.005 mol), 2,2'-bipyridine (1.56 g, 0.01 mol), K2CO3 (2.76 g, 0.02 mol) and DMF (50 mL) were added into a stirred 250 mL stainless steel reactor. The temperature was raised to 120°C for reaction for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and an aqueous solution (50 mL) of NaOH (4.0 g, 0.1 mol) was added. The mixture was heated to reflux for reaction for 12 hours. After the reaction was completed by TLC detection, an organic solvent, ethyl acetate (50 mL), was added for separation. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was recovered by vacuum distillation. The crude product was subjected to vacuum distillation to obtain pure 1-nitro-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene (1.85 g, yield 85.3%, purity 99.1%).
[0061] 1H NMR (400MHz, CDCl3): δ8.28-8.23(m,2H), 7.67-7.60(m,2H), 6.15(q,J=1.5Hz,1H), 5.93(q,J=1.7Hz,1H).
[0062] Example 6
[0063] In an inert atmosphere, 4-chlorobromobenzene (1.91 g, 0.01 mol), 4,4,4-trifluoro-2-butynoic acid (4.14 g, 0.03 mol), CuI (0.95 g, 0.005 mol), 2,2'-bipyridine (1.56 g, 0.01 mol), K2CO3 (2.76 g, 0.02 mol) and ethylene glycol dimethyl ether (50 mL) were added to a stirred 250 mL stainless steel reactor. The temperature was raised to 150°C for 10 hours. After the reaction, the mixture was cooled to room temperature, and an aqueous solution (50 mL) of NaOH (4.0 g, 0.1 mol) was added. The mixture was heated to reflux for 12 hours. After the reaction was completed by TLC, an organic solvent, ethyl acetate (50 mL), was added for separation. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was recovered by vacuum distillation. The crude product was subjected to vacuum distillation to obtain pure 1-chloro-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene (1.51 g, yield 79.1%, purity 99.3%). 1H NMR (400 MHz, CDCl3): δ7.41-7.34 (m, 4H), 5.98 (q, J = 1.4 Hz, 1H), 5.77 (q, J = 1.7 Hz, 1H).
[0064] Example 7
[0065] In an inert atmosphere, 3,5-dichlorobromobenzene (22.6 g, 0.1 mol), 4,4,4-trifluoro-2-butynoic acid (41.4 g, 0.3 mol), CuI (0.19 g, 0.001 mol), 2,2'-bipyridine (0.312 g, 0.002 mol), K2CO3 (27.6 g, 0.2 mol) and 1.2-dichloroethane (500 mL) were added to a stirred 2.5 L stainless steel reactor. The temperature was raised to 80°C for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, and an aqueous solution (500 mL) of NaOH (40 g, 1.0 mol) was added. The mixture was heated to reflux for 12 hours. After the reaction was completed by TLC, an organic solvent, dichloromethane (500 mL), was added for separation. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was recovered by vacuum distillation. The crude product was subjected to vacuum distillation to obtain pure 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (20.5 g, yield 85.1%, purity 99.6%). 1H NMR (400 MHz, CDCl3): δ7.41 (s, 1H); 7.39 (s, 1H), 7.33 (s, 1H), 6.05 (s, 1H), 5.82 (s, 1H).
[0066] Example 8
[0067] In an inert atmosphere, 3,4,5-trichloroiodobenzene (30.7 g, 0.1 mol), 4,4,4-trifluoro-2-butynoic acid (41.4 g, 0.3 mol), CuI (1.9 g, 0.01 mol), 2,2'-bipyridine (3.12 g, 0.02 mol), K2CO3 (27.6 g, 0.2 mol) and 1.2-dichloroethane (500 mL) were added to a stirred 2.5 L stainless steel reactor. The temperature was raised to 80°C for 24 hours. After the reaction, the mixture was cooled to room temperature, and an aqueous solution (500 mL) of NaOH (40 g, 1.0 mol) was added. The mixture was heated to reflux for 12 hours. After the reaction was completed by TLC, an organic solvent, dichloromethane (500 mL), was added for separation. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was recovered by vacuum distillation. The crude product was subjected to vacuum distillation to obtain pure 1,2,3-trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (22.8 g, yield 82.9%, purity 99.5%). 1H NMR (400 MHz, CDCl3): δ7.46 (s, 2H), 6.05 (s, 1H), 5.82 (s, 1H).
[0068] In summary, the aryl halide, polar solvent, 4,4,4-trifluoro-2-butynoic acid, base, copper catalyst and ligand used in the present invention are all industrial products, cheap and easy to obtain, and the present invention also has the advantages of short reaction steps and high production efficiency. The trifluoromethyl-substituted aryl ethylene obtained by the synthesis method has a high reaction yield, and a product with a purity of ≥99.0% can be obtained with a yield of more than 70%. The operation is simple, and the low-cost process is very suitable for industrialization and can be widely promoted and used.
[0069] The above description is only a preferred embodiment of the present invention. It should be pointed out that, for ordinary technicians in this field, several modifications and improvements can be made without departing from the creative concept of the present invention, and these should also be regarded as within the scope of protection of the invention.
Claims
1. A method for synthesizing a trifluoromethyl-substituted arylethylene compound, characterized in that: The following steps are involved: S1. Under an inert atmosphere, an aryl halide, 4,4,4-trifluoro-2-butynoic acid, a catalyst, a ligand, and a base are reacted in a solvent to obtain an intermediate 1; S2. Add an inorganic base to carry out a decarboxylation reaction to obtain a trifluoromethyl-substituted arylethylene compound.
2. The method for synthesizing a trifluoromethyl-substituted aryl vinyl compound according to claim 1, characterized in that: The synthetic route is as follows: Wherein: R1 is selected from 1 to 5 of the following substituents, and the multiple substituents may be the same substituent or different substituents. The substituents are respectively hydrogen, C1-C6 alkyl, phenolic hydroxyl, C1-C6 alkoxy, trifluoromethyl, nitro, halogen, amino, C1-C6 alkyl substituted amino, C1-C6 alkyl substituted mercapto, C1-C6 alkyl substituted sulfoxide or C1-C6 alkyl substituted sulfone.
3. The method for synthesizing a trifluoromethyl-substituted aryl vinyl compound according to claim 1, characterized in that: In step S1, the solvent is a polar solvent, and the polar solvent includes any one of dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, tetrahydrofuran, dioxane, acetone, acetonitrile, ethylene glycol dimethyl ether, toluene, xylene, N,N-dimethylformamide, and N,N-dimethylacetamide; in step S1, the catalyst includes CuCl, CuBr, Cu(MeCN )4 Any one of PF6, CuI, CuCN, Cu2O.
4. The method for synthesizing a trifluoromethyl-substituted aryl vinyl compound according to claim 1, characterized in that: In step S1, the ligand includes any one of 1,10-phenanthroline, 2,2'-bipyridine, 4,4'-dimethoxy-2,2'-bipyridine, 6,6'-dimethyl-2,2'-bipyridine, terpyridine or N-methylpyrrolidone; the base includes any one of triethylamine, K2CO3, Cs2CO3, pyridine, DBU, and diisopropylethylamine.
5. The method for synthesizing a trifluoromethyl-substituted aryl vinyl compound according to claim 1, characterized in that: In step S1, the molar ratio of the aryl halide to 4,4,4-trifluoro-2-butynoic acid is 1:1.5-3; the molar ratio of the aryl halide to the catalyst is 1:0.01-0.5; the molar ratio of the aryl halide to the ligand is 1:0.02-1; and the molar ratio of the aryl halide to the base is 1:1.0-2.
0.
6. The method for synthesizing a trifluoromethyl-substituted aryl vinyl compound according to claim 1, characterized in that: The reaction temperature in step S1 is -20-200°C; the decarboxylation reaction temperature in step S2 is 50-200°C.
7. The method for synthesizing a trifluoromethyl-substituted aryl vinyl compound according to claim 1, characterized in that: In step S2, the inorganic base includes any one of NaOH, KOH, LiOH, Ca(OH)2, Na2CO3, K2CO3, NaHCO3, KHCO3, and Cs2CO3.
8. The method for synthesizing a trifluoromethyl-substituted aryl vinyl compound according to claim 1, characterized in that: Step S2 also includes a post-treatment step after the decarboxylation reaction, specifically: liquid separation extraction, recovery of organic solvent, and reduced pressure distillation.