Preparation method of (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) arene compound
By using nickel catalyst under an inert gas atmosphere, the synthesis process of α-trifluoromethyl tertiary alkyl aromatics is simplified, the problems of complex synthesis and limited structure in the prior art are solved, and low-cost and efficient Preparation method improves product yield and process simplicity.
Patent Information
- Application Number
- CN202310834969.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-07-07
- Publication Date
- 2025-01-07
- Estimated Expiration
- Not applicable · inactive patent
AI Technical Summary
The existing synthesis methods of α-trifluoromethyl tertiary alkyl substituted aromatic hydrocarbons are complex and have limited structures, and there is a lack of effective preparation methods based on simple and easy-to-get raw materials.
The reaction was carried out under an inert gas atmosphere using 2-aryl-3,3,3-trifluoropropylene, bromomethylaromatic, manganese powder and nickel catalyst at a specific molar ratio, and prepared by nickel catalytic method (1-aryl) catalytic method (1-aryl) catalytic method Methyl-3-aryl-1-trifluoromethylpropyl)aromatic compounds simplify the process flow and improve product yield.
The preparation of α-trifluoromethyl tertiary alkyl aromatic compounds with low cost and simplified process is achieved, eliminating cumbersome prefunctionalization steps, and improving product yield and process simplicity.
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Abstract
Description
Technical Field
[0001] The invention belongs to the technical field of organic chemical synthesis, and specifically relates to a method for preparing a (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound. Background Art
[0002] The introduction of trifluoromethyl groups into organic compounds can significantly change their physical and chemical properties and biological activities. Therefore, more and more trifluoromethyl-containing compounds are widely used in the fields of pesticides, medicine and material chemistry. Especially in recent decades, the methods of constructing trifluoromethyl-containing structures have attracted widespread attention from scientists. However, among the reported synthetic methods, the synthesis of α-trifluoromethyl tertiary alkyl substituted aromatic compounds is relatively rare, although such structures have achieved important applications in the field of medicine. For example, the anticancer drugs agorafenib and apellis are both 1-methyl-1-trifluoromethyl-ethyl substituted aromatic compounds.
[0003] At present, there are mainly the following strategies for synthesizing α-trifluoromethyl tertiary alkyl substituted aromatics. First, as disclosed in document 1 (Tsuchida, K.; Senda, Y.; Nakajima, K.; Nishibayashi, Y. Angew. Chem. Int. Ed. 2016, 55, 9728-9732), a cross-coupling reaction is carried out by using trifluoromethyl substituted propargyl ester and electron-rich heterocyclic compound under copper catalysis. The specific reaction process is as follows:
[0004]
[0005] Secondly, as disclosed in document 2 (Vayer, M.; Mayer, RJ; Moran, J.; Leboeuf, D.ACS Catal. 2022, 12, 10995-11001), α-trifluoromethyl-β-nitrostyrene is used as a raw material, and the electron-rich heterocyclic aromatic hydrocarbon is subjected to Friedel-Crafts alkylation under the catalysis of a chiral Lewis acid. The specific reaction process is as follows:
[0006]
[0007] Third, in the method disclosed in document 3 (Punna, N.; Harada, K.; Shibata, N. Chem. Commun. 2018, 54, 7171-7174), 2,2-diaryl-1,1,1-trifluoro-2-chloroethane is used as a raw material to carry out a Stille coupling reaction under palladium catalysis. The specific reaction process is as follows:
[0008]
[0009] Fourthly, in the method disclosed in document 4 (Vayer, M.; Mayer, RJ; Moran, J.; Leboeuf, D.ACS Catal. 2022, 12, 10995-11001), 1-aryl-1-trifluoromethyl allene is used as a raw material and a hydromethylation reaction is carried out under iridium catalysis. The specific reaction process is as follows:
[0010]
[0011] However, these strategies all have their own shortcomings, such as the complex synthesis of trifluoromethyl-containing raw materials, the limited substrate range and the obtained α-trifluoromethyl tertiary alkyl structure, etc.
[0012] Therefore, it is still of great significance to develop new methods for synthesizing α-trifluoromethyl tert-alkyl aromatic compounds based on simple and readily available raw materials. Summary of the invention
[0013] The purpose of the present invention is to provide a method for synthesizing (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic hydrocarbons to overcome the deficiencies of the prior art. The chemical structural formula of the compound is as follows:
[0014]
[0015] In formula (I), Ar 1 Any one of the following groups: 4-nitrilephenyl, 4-benzyloxycarbonylphenyl, 4-methanesulfonylphenyl, 4-trifluoromethylphenyl, 4-bromophenyl, 4-chlorophenyl, 3-methoxy-4-fluorophenyl, 3-(N-acetylamino)phenyl, 3-nitrilepyridin-5-yl, 2,6-dichloropyridin-5-yl, quinolin-3-yl, 4-methoxyphenyl, naphth-2-yl, benzofuran-5-yl;
[0016] Ar 2 Any one of the following groups is selected: phenyl, 4-methoxyphenyl, 4-acetoxyphenyl, 3-methoxycarbonylphenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 3,4-dichlorophenyl, 4-bromophenyl, 4-iodophenyl, naphth-1-yl, thiophen-3-yl, benzofuran-3-yl.
[0017] In order to solve the above technical problems, the present invention provides the following technical solution: a method for preparing a (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound, the method comprising the following steps:
[0018] Under an inert gas atmosphere, 2-aryl-3,3,3-trifluoropropene, bromomethyl aromatic hydrocarbon, manganese powder, nickel catalyst, and ligand are sequentially added to a solvent to obtain a mixture, wherein the molar ratio of 2-aryl-3,3,3-trifluoropropene, bromomethyl aromatic hydrocarbon, manganese powder, nickel catalyst, and ligand is 1:4-6:2-3:0.1:0.12;
[0019] The mixture is reacted at -10 to 0° C. under an inert gas atmosphere, and the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl)arene compound is collected from the reaction product.
[0020] As a preferred embodiment of the method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic hydrocarbon compound of the present invention, the 2-aryl-3,3,3-trifluoropropene is 2-(4-nitrile phenyl)-3,3,3-trifluoropropene, 2-(4-benzyloxycarbonylphenyl)-3,3,3-trifluoropropene, 2-(4-methylsulfonylphenyl)-3,3,3-trifluoropropene, 2-(4-trifluoromethylphenyl)-3,3,3-trifluoropropene, 2-(4-bromophenyl)-3,3,3-trifluoropropene, 2-(4-chlorophenyl)-3,3,3-trifluoropropene. olefins, 2-(3-methoxy-4-fluorophenyl)-3,3,3-trifluoropropene, 2-(3-(N-acetylamino)phenyl)-3,3,3-trifluoropropene, 2-(3-nitrile pyridin-5-yl)-3,3,3-trifluoropropene, 2-(2,6-dichloropyridin-5-yl)-3,3,3-trifluoropropene, 2-(quinolin-3-yl)-3,3,3-trifluoropropene, 2-(4-methoxyphenyl)-3,3,3-trifluoropropene, 2-(naphthalen-2-yl)-3,3,3-trifluoropropene, 2-(benzofuran-5-yl)-3,3,3-trifluoropropene.
[0021] As a preferred embodiment of the method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound of the present invention, the bromomethyl aromatic compound is bromomethylbenzene, 1-bromomethyl-4-methoxybenzene, 1-bromomethyl-4-acetoxybenzene, 1-methoxycarbonyl-3-bromomethylbenzene, 1-trifluoromethyl-4-bromomethylbenzene, 1-bromomethyl-4-trifluoromethoxybenzene, 1-bromomethyl-3,4-dichlorophenyl, 1-bromomethyl-4-bromophenyl, 1-bromomethyl-4-iodophenyl, 1-bromomethylnaphthalene, 3-bromomethylthiophene, and 3-bromomethylbenzofuran.
[0022] As a preferred embodiment of the method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic hydrocarbon compound of the present invention, the nickel catalyst is NiBr2·DME.
[0023] As a preferred embodiment of the method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic hydrocarbon compound of the present invention, the ligand is 6,6′-dimethyl-2,2′-bipyridine.
[0024] As a preferred embodiment of the method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic hydrocarbon compound of the present invention, the reaction temperature is 0°C.
[0025] As a preferred embodiment of the method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic hydrocarbon compound of the present invention, the solvent is tetrahydrofuran.
[0026] As a preferred embodiment of the method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic hydrocarbon compound of the present invention, the inert gas is at least one of nitrogen and argon.
[0027] As a preferred embodiment of the method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic hydrocarbon compound of the present invention, the reaction time is 18 to 36 hours.
[0028] Beneficial effects of the present invention:
[0029] (1) The present invention provides a method for preparing a (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound, wherein the raw materials used are low in cost and easy to obtain; at the same time, the cumbersome pre-functionalization step is eliminated;
[0030] (2) The present invention proposes for the first time a method for preparing a (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound, which is a new method for preparing a synthetic α-trifluoromethyl tertiary alkyl aromatic compound, which eliminates the cumbersome functionalization steps and simplifies the process while optimizing the temperature, solvent, ligand, and catalyst to achieve the best product yield. BRIEF DESCRIPTION OF THE DRAWINGS
[0031] In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the following briefly introduces the drawings required for describing the embodiments. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without creative labor. Among them:
[0032] Figure 1 It is the H NMR spectrum of 3a in Example 3 of the present invention.
[0033] Figure 2 It is the NMR carbon spectrum of 3a in Example 3 of the present invention.
[0034] Figure 3 It is the NMR fluorine spectrum of 3a in Example 1 of the present invention.
[0035] Figure 4 This is the H NMR spectrum of 31 in Example 1 of the present invention.
[0036] Figure 5 This is the NMR carbon spectrum of 31 in Example 1 of the present invention.
[0037] Figure 6 This is the NMR fluorine spectrum of 31 in Example 1 of the present invention.
[0038] Figure 7 This is the H NMR spectrum of 3o in Example 1 of the present invention.
[0039] Figure 8 This is the NMR carbon spectrum of 3o in Example 1 of the present invention.
[0040] Fig. 9 This is the NMR fluorine spectrum of 3o in Example 1 of the present invention. DETAILED DESCRIPTION
[0041] In order to make the above-mentioned objects, features and advantages of the present invention more obvious and easy to understand, the specific implementation methods of the present invention are described in detail below in conjunction with the embodiments of the specification.
[0042] In the following description, many specific details are set forth to facilitate a full understanding of the present invention, but the present invention may also be implemented in other ways different from those described herein, and those skilled in the art may make similar generalizations without violating the connotation of the present invention. Therefore, the present invention is not limited to the specific embodiments disclosed below.
[0043] Secondly, the term "one embodiment" or "embodiment" as used herein refers to a specific feature, structure, or characteristic that may be included in at least one implementation of the present invention. The term "in one embodiment" that appears in different places in this specification does not necessarily refer to the same embodiment, nor does it refer to a separate or selective embodiment that is mutually exclusive with other embodiments.
[0044] Embodiment 1:
[0045]
[0046] (1) Under nitrogen atmosphere, 0.2 mmol 2-(4-cyanophenyl)-3,3,3-trifluoropropene, 0.6 mmol tert-butyl bromide, 0.4 mmol manganese powder, 0.02 mmol NiBr 2 DME and 0.024 mmol of 6,6′-dimethyl-2,2′-bipyridine were added to 1.0 mL of tetrahydrofuran in sequence to obtain a mixture;
[0047] (2) Under a nitrogen atmosphere, the mixture was stirred at 0°C for 18 hours, and 4-(1-benzyl-3-phenyl-1-trifluoromethylpropyl)benzonitrile 3a (63.7 mg, 0.17 mmol, colorless oil) was collected from the product with a yield of 84%.
[0048] 1 H NMR (400 MHz, CDCl 3 ): δ7.70 (d, J=8.5Hz, 2H), 7.53 (d, J=8.5Hz, 2H), 7.35-7.28 (m, 2H), 7.25-7.09 (m, 6H), 6.78 (d, J=6.8Hz, 2H ), 3.29 (s, 2H), 2.73 (ddd, J=13.3, 13.3, 5.5Hz, 1H), 2.54 (ddd, J=13.3, 13.3, 4.2Hz, 1H), 2.41-2.22 (m, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ142.5, 141.3, 134.4, 132.2, 130.8, 129.1 (q, J=1.9Hz), 128.8, 128.2, 128.1, 128.0 (q, J=286. 1Hz), 127.3, 126.4, 118.5, 111.9, 53.5 (q, J=22.6Hz), 42.5 (q, J=2.3Hz), 34.6, 30.4 (q, J=1.6Hz). 19 F NMR (376 MHz, CDCl 3 ): δ-66.08 (s, 3F).HRMS (ESI, m / z): calcd for C 24 H 21 F 3 N, [M+H] + :380.1626, found:380.1624.
[0049] Embodiments 2 to 11
[0050] Embodiments 2 to 11 are substantially the same as Embodiment 1, except that:
[0051] Table 1 Examples 2 to 11
[0052]
[0053]
[0054] Embodiment 12:
[0055]
[0056] (1) Under nitrogen atmosphere, 0.2 mmol 2-(4-methoxyphenyl)-3,3,3-trifluoropropene, 1.2 mmol bromomethylbenzene, 0.6 mmol manganese powder, 0.02 mmol NiBr 2 DME and 0.024 mmol 6,6′-dimethyl-2,2′-bipyridine were added to 1.0 mL tetrahydrofuran in sequence to obtain a mixture;
[0057] (2) Under nitrogen atmosphere, the mixture was stirred at -10 °C for 36 h, and 4-(1-benzyl-3-phenyl-1-trifluoromethylpropyl)anisole 31 (43.8 mg, 0.11 mmol, colorless oil) was collected from the product with a yield of 57%.
[0058] 1 H NMR (400 MHz, CDCl 3 ): δ8.24-8.17 (m, 1H), 7.62 (dd, J=8.8, 2.4Hz, 1H), 7.31-7.27 (m, 3H), 7.24-7.15 (m, 4H), 7.11 (d, J=7.2Hz, 2 H), 6.91-6.82 (m, 2H), 6.79 (d, J=8.9Hz, 1H), 3.98 (s, 3H), 3.27 (s, 2H), 2.77-2.54 (m, 2H), 2.32-2.15 (m, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ163.4, 146.7, 141.5, 138.7 (q, J=1.6Hz), 134.9, 130.9, 128.7, 128.3 (q, J=286.0Hz), 128.1, 1 27.1, 126.3, 125.4, 110.6, 53.6, 51.0 (q, J=22.8Hz), 41.6 (q, J=2.3Hz), 34.0, 30.4 (q, J=1.6Hz). 19 F NMR (376 MHz, CDCl 3 ): δ-67.43(s, 3F).HRMS(ESI, m / 2): calcd for C 24 H 24 F 3 O, [M+H] + :385.1779, found:385.1777.
[0059] Embodiment 13, 14
[0060] Embodiments 13 and 14 are substantially the same as embodiment 12, except that:
[0061] Table 2 Examples 13 and 14
[0062]
[0063] Embodiment 15:
[0064]
[0065] (1) Under a nitrogen atmosphere, 0.2 mmol of 2-(4-cyanophenyl)-3,3,3-trifluoropropene, 1.2 mmol of 4-bromomethyl-anisole, 0.4 mmol of manganese powder, 0.01 mmol of NiBr2·DME, and 0.012 mmol of 6,6′-dimethyl-2,2′-bipyridine were sequentially added to 1.0 mL of tetrahydrofuran to obtain a mixture;
[0066] (2) Under nitrogen atmosphere, the mixture was stirred at 0°C for 36 h, and 4-(1-(4-methoxybenzyl)-3-(4-methoxyphenyl)-1-trifluoromethylpropyl)benzonitrile 3o (59.8 mg, 0.14 mmol, colorless oil) was collected from the product with a yield of 68%.
[0067] 1 H NMR (400 MHz, CDCl 3 ): δ7.66 (d, J=8.6Hz, 2H), 7.48 (d, J=8.5Hz, 2H), 7.01 (d, J=8.6Hz, 2H), 6.82 (d, J=8.6Hz, 2H), 6.72-6.55 (m, 4H), 3.78 (s, 3 H), 3.74 (s, 3H), 3.17 (s, 2H), 2.62 (ddd, J=13.2, 13.2, 5.4Hz, 1H), 2.43 (ddd, J=13.2, 13.2, 4.2Hz, 1H), 2.31-2.12 (m, 2H). 19 F NMR (376 MHz, CDCl 3 ): δ-66.02 (s, 3F). 13 C NMR (100 MHz, CDCl 3 ): δ158.7, 158.2, 142.6, 133.4, 132.2, 131.8, 129.1, 129.1, 128.2 (q, J=286.3Hz), 126.2, 118.5, 114.1, 113.5, 111.7, 55.4, 55.2, 53.4 (q, J=22.4Hz), 41.7, 34.8, 29.5.HRMS (ESI, m / z): calcdfor C 26 H25 F 3 NO 2 , [M+H] + :440.1837, found:440.1831.
[0068] Embodiments 16 to 25
[0069] Examples 16 to 25 are substantially the same as Example 15, except that:
[0070] Table 3 Examples 16 to 25
[0071]
[0072]
[0073] Embodiment 26:
[0074] (1) The effect of controlling different reaction temperatures on yield:
[0075]
[0076] The reactions were all carried out in tetrahydrofuran (1 mL) on a scale of 1a (0.2 mmol) and 2a (0.6 mmol). The temperature conditions and reaction results are shown in Table 4.
[0077] Table 4
[0078]
[0079]
[0080] It can be seen from Table 4 that the reaction can be carried out at -10°C to room temperature, with 0°C being the best choice.
[0081] (2) Control the effect of different solvents on yield:
[0082]
[0083] The reactions were all carried out in a solvent (1 mL) at 0°C using 1a (0.2 mmol) and 2a (0.6 mmol). The solvent conditions and reaction results are shown in Table 5.
[0084] Table 5
[0085]
[0086] It can be seen from Table 5 that THF is the best choice.
[0087] (3) The effect of different 2a equivalents on the yield is:
[0088]
[0089] The reactions were all carried out in THF (1 mL) at 0°C using 1a (0.2 mmol) and 2a (0.4 mmol to 1.2 mmol). The reaction results are shown in Table 6.
[0090] Table 6
[0091]
[0092] It can be seen from Table 6 that 4 equivalents of 2a are the best choice.
[0093] (3) The effect of different ligands on the yield is:
[0094]
[0095] The reactions were carried out in THF (1 mL) at 0°C using 1a (0.2 mmol) and 2a (0.8 mmol). The reaction results are shown in Table 7.
[0096] Table 7
[0097]
[0098]
[0099] It can be seen from Table 7 that 6,6'-dimethyl-2,2'-bipyridine is the best choice.
[0100] The present invention proposes for the first time a method for preparing a (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound, which is a new method for preparing a synthetic α-trifluoromethyl tertiary alkyl aromatic compound, which eliminates the cumbersome functionalization steps, simplifies the process, optimizes solvents, ligands, and catalysts, and achieves the best product yield.
[0101] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention rather than to limit it. Although the present invention has been described in detail with reference to the preferred embodiments, those skilled in the art should understand that the technical solutions of the present invention may be modified or replaced by equivalents without departing from the spirit and scope of the technical solutions of the present invention, which should all be included in the scope of the claims of the present invention.
Claims
1. A (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound, characterized in that: The chemical structure of the compound is as follows: in, Ar 1 4-nitrilephenyl, 4-benzyloxycarbonylphenyl, 4-methanesulfonylphenyl, 4-trifluoromethylphenyl, 4-bromophenyl, 4-chlorophenyl, 3-methoxy-4-fluorophenyl, 3-(N-acetylamino)phenyl, 3-nitrilepyridin-5-yl, 2,6-dichloropyridin-5-yl, quinolin-3-yl, 4-methoxyphenyl, naphth-2-yl, benzofuran-5-yl; Ar 2 It is phenyl, 4-methoxyphenyl, 4-acetoxyphenyl, 3-methoxycarbonylphenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 3,4-dichlorophenyl, 4-bromophenyl, 4-iodophenyl, naphth-1-yl, thiophen-3-yl, benzofuran-3-yl.
2. The method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound according to claim 1, characterized in that: include, Under an inert gas atmosphere, 2-aryl-3,3,3-trifluoropropene, bromomethyl aromatic hydrocarbon, manganese powder, nickel catalyst and ligand are sequentially added into a solvent to obtain a mixture, wherein the molar ratio of 2-aryl-3,3,3-trifluoropropene, bromomethyl aromatic hydrocarbon, manganese powder, nickel catalyst and ligand is 1:4-6:2-3:0.1:0.12; The mixture was reacted at -10 to 0°C under an inert gas atmosphere, and (1-arylmethyl-3-aryl-1-trifluoromethylpropyl)arene was collected from the reaction solution.
3. The method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound according to claim 2, characterized in that: The 2-aryl-3,3,3-trifluoropropene is 2-(4-nitrilephenyl)-3,3,3-trifluoropropene, 2-(4-benzyloxycarbonylphenyl)-3,3,3-trifluoropropene, 2-(4-methylsulfonylphenyl)-3,3,3-trifluoropropene, 2-(4-trifluoromethylphenyl)-3,3,3-trifluoropropene, 2-(4-bromophenyl)-3,3,3-trifluoropropene, 2-(4-chlorophenyl)-3,3,3-trifluoropropene, 2-(3-methoxy-4-fluorophenyl)-3,3,3-trifluoropropene. Trifluoropropene, 2-(3-(N-acetylamino)phenyl)-3,3,3-trifluoropropene, 2-(3-nitrilepyridin-5-yl)-3,3,3-trifluoropropene, 2-(2,6-dichloropyridin-5-yl)-3,3,3-trifluoropropene, 2-(quinolin-3-yl)-3,3,3-trifluoropropene, 2-(4-methoxyphenyl)-3,3,3-trifluoropropene, 2-(naphthalen-2-yl)-3,3,3-trifluoropropene, 2-(benzofuran-5-yl)-3,3,3-trifluoropropene.
4. The method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound according to claim 2, characterized in that: The bromomethyl aromatics are bromomethylbenzene, 1-bromomethyl-4-methoxybenzene, 1-bromomethyl-4-acetoxybenzene, 1-methoxycarbonyl-3-bromomethylbenzene, 1-trifluoromethyl-4-bromomethylbenzene, 1-bromomethyl-4-trifluoromethoxybenzene, 1-bromomethyl-3,4-dichlorophenyl, 1-bromomethyl-4-bromophenyl, 1-bromomethyl-4-iodophenyl, 1-bromomethylnaphthalene, 3-bromomethylthiophene, and 3-bromomethylbenzofuran.
5. The method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound according to claim 2, characterized in that: The nickel catalyst is NiBr2·DME.
6. The method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound according to claim 2, characterized in that: The ligand is 6,6'-dimethyl-2,2'-bipyridine.
7. The method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound according to claim 2, characterized in that: The reaction temperature is -10 to 0°C.
8. The method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound according to claim 2, characterized in that: The solvent is tetrahydrofuran.
9. The method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound according to claim 2, characterized in that: The inert gas is at least one of nitrogen and argon.
10. The method for preparing the (1-arylmethyl-3-aryl-1-trifluoromethylpropyl) aromatic compound according to claim 2, characterized in that: The reaction time is 18 to 36 hours.
Citation Information
Patent Citations
Preparation method of 2, 2-disubstituted-1, 1, 1-trifluoroethane compound
CN114835565A