Synthesis and application of beta-borate-beta-chloro ester compound

Abstract

The invention provides a method for synthesizing a beta-borate-beta-chloro ester compound, which comprises the following steps: by taking 1-aryl alkenyl borate, an alcohol compound and oxalyl chloride as raw materials and a metal ruthenium compound as a photocatalyst, adding an additive, reacting in an organic solvent in N2 atmosphere at room temperature under visible light for 40-50 hours, and carrying out reduced pressure distillation to remove the solvent, thereby obtaining the beta-borate-beta-chloro ester compound. And separating and purifying to obtain a target product. The synthesized beta-boric acid ester-beta-chlorine ester compound can be used for synthesizing a drug intermediate 3-pinacol boric acid-3-aryl acrylate. The method has the advantages of cheap and easily available reaction raw materials, mild conditions, simple operation, small environmental pollution, fast reaction rate, simple post-treatment, high product yield and good purity, and is suitable for industrial production.

Description

Technical Field

[0001] The present invention relates to a β -Borate Esters- β The invention discloses a synthesis method and application of chloroester compounds, belonging to the technical field of synthetic chemistry. Background Art

[0002] As an important and universal synthetic skeleton in synthetic chemistry, organoboron compounds have rich derivative transformation capabilities and have shown great application value in organic synthesis. They have long been highly favored by chemists. In particular, β -Boryl carbonyl compounds are a class of stable, low-toxic organic boron compounds that are easily converted into a variety of biologically active molecules and have shown unique charm in synthetic applications. β -Borate Esters- β -Chlorocarbonyl compounds are multifunctional compounds, including two hot research segments: one is α -halogenated borate structure; secondly, β -boryl-carbonyl structure.

[0003] (one) α -Synthesis method of halogenated borate ester structure Current build α -Halogenated borate esters method including halogenation-alkylation of alkenyl borate esters (a) Zhao, Y.; Yang, Z.; Wang, X.; Kang, Q.; Wang, B.; Wu, T.; Lei, H.; Ma, P.; Su, W.; Wang, S.; Wu, Z.; Huang, X.; Fan, C.; Wei, X.Mechanochemical Synthesis of α -halo Alkylboronic Esters. Adv. Sci .2024, 2404071; b) Li, B.; Bunescu, A.;Gaunt, MJ Multicomponent synthesis of α -chloro alkylboronic esters viavisible-light-mediated dual catalysis, Chem ,2023, 9, 216; c) Ho, TD; Lee , BJ ; Tan , C. ; Utley , JA ; Ngo, NQ; Hull, KL Efficient Synthesis of α-Haloboronic Esters via Cu-Catalyzed Atom TransferRadical Addition, 1999; J. Am. Chem. Soc. 2023, 145 , 27230) (a) Fang, T.; Wang, L.; Wu , M. ;Qi , X. ; Liu, C. Diborodichloromethane as a Versatile Reagent for ChemodivergentSynthesis of Gem-Diboryl Alkanes, Angew. Chem. Int. Ed .2024, 63 , e202315227; (b)Water, C.-L.; Chen , H. ; Gao, Q.; Han, J.; Lee, We.; Xie, J. Dinuclear Gold-Catalyzed DivergentDechlorinative Radical Borylation of Gem-Dichloroalkanes. Nat. Commun .2024, 15 , 3721) α -power(a) LaPorte, AJ;Feldner, JE; Spies , JC ; Maher , TJ ; Burke, MD MIDA- and TIDA-Boronates Stabilize α-Radicals Through B−NHyperconjugation, 1999 . Angew. Chem. Int. Ed .2023, 62 , e202309566.b)Gao, F.-C.; Li, M.; Gu, H.-Y; Chen , X.-Y. ; Xu , S. ;Wei , Y. ; Hong, K. Construction of α -Halogenated Boronic Esters via VisibleLight-Induced C–H Bromination, J. Org. Chem .2023, 88 , 14246) and halogenation of geminal diboron esters (a) Ning, P.-F.; Wei, Y.; Chen, X.-Y.; Yang, Y.-F.; Gao, F.-C.; Hong, K. AGeneral Method to Access Sterically Encumbered GeminalBis(boronates) viaFormal Umpolung Transformation of Terminal Diboron Compounds, Angew. Chem. Int. Ed .2024, 63 , e202315232. b) Liao, S.; Liang, J.; Li, C.; Chen, N.; Yang,K.; Chen, J.; Song,Q. Synthesis of α -Haloboronates by the Halogenation of gem-Diborylalkanes via Tetracoordinate Boron Species, Org. Lett. 2023, 25 , 2928).

[0004] (two) β - Synthesis method of boryl-carbonyl structure Current build β -boryl-carbonyl structure strategy mainly includes carbonyl radical and vinyl boron addition (Nagaraju, A.; Saiaede, T.; Eghbarieh, N.; Masarwa, A. Photoredox-Mediated Deoxygenative Radical Additions of Aromatic Acids to VinylBoronic Esters and gem-Diborylalkenes, Chem. Eur. J .2023, 29 , e202202646) and transition metal-catalyzed coupling of alkenylboranes with carbonyl derivatives (Wilhelmsen, CA; Zhang, X.; Myhill, JA; Morken, JPEnantioselective Synthesis of Tertiary β-Boryl Amides by Conjunctive Cross-Coupling of Alkenyl Boronates and Carbamoyl Chlorides, Angew. Chem. Int. Ed. 2022, 61 , e202116784), and the substrate universality is not very wide.

[0005] (three) β -Borate- β - Synthesis method of chloroester compounds Current build β -Borate- β -Chloroesters have only one strategy, namely β -Carbonyl esters catalyzed by copper Carbonyl deoxyhalogenation-boration reaction, and this method only synthesized three substrates (Wang, D.; Zhou, J.; Hu, Z.; Xu, T. Deoxygenative Haloboration and Enantioselective Chloroboration of Carbonyls, J. Am. Chem. Soc. 2022, 144 , 22870).

[0006] In summary, despite α -There are many methods for synthesizing halogenated borate ester structures, but β -Borate Esters- β -Chloroester compounds have only one synthesis method, with only two substrates, high cost and complicated operation. Summary of the invention

[0008] The technical problem to be solved by the present invention is to provide a novel method for preparing a novel nanostructured carbon nanotube with low cost, easy-to-obtain raw materials, strong operability, green environmental protection, and wide substrate universality. β -Borate Esters- β -The synthesis method of chloroester compounds has the potential to be applied to industrial production. β -Borate Esters- β -Chloroester compounds can be used to synthesize drug intermediates.

[0009] The present invention β -Borate Esters- β- A method for synthesizing chloroester compounds, using 1-aryl alkenyl borate, alcohol compounds and oxalyl chloride as raw materials, a metal ruthenium compound as a photocatalyst, adding additives, reacting in an organic solvent under a N2 atmosphere, under a 25-35W blue light lamp at room temperature for 40-50 hours, removing the solvent by distillation under reduced pressure, and separating and purifying to obtain the target product; The synthetic route is as follows: Where: R 1 Any one selected from hydrogen, halogen, cyano, ester, sulfonyl, amide, alkoxy, alkyl with a carbon chain length of C1 to C10, and aryl; R 2 is an alkyl group with a carbon chain length of C1 to C8; R 3 The primary alkyl group, secondary alkyl group or tertiary alkyl group with a carbon chain length of C1 to C16, wherein the primary alkyl group includes but is not limited to methyl, ethyl, n-propyl, n-butyl, perfluorohexylethyl, and n-hexadecyl group, the secondary alkyl group includes but is not limited to isopropyl, cyclobutyl, cyclohexyl, cyclododecyl, and 2-adamantyl group, and the tertiary alkyl group includes 1-adamantyl group.

[0010] Preferably, β -Borate Esters- β -Chloroester compounds have the structural formula: Preferably, the structural formula of 1-aryl alkenyl borate is: The alcohol compound is a primary alcohol, a secondary alcohol or a tertiary alcohol. The primary alcohol includes methanol, ethanol, propanol and butanol; the secondary alcohol includes isopropanol, cyclohexanol and menthol; the tertiary alcohol includes 1-adamantanol and tert-butanol.

[0011] The additive is any one of an alkyl tertiary amine, an aryl tertiary amine, a thiol, a thiophenol, and a Hans ester; and the amount of the additive is 1.5 times the molar amount of the 1-aryl alkenyl borate.

[0012] The organic solvent is acetonitrile, dichloromethane, 1,2-dichloroethane, 1,4-dioxane, tetrahydrofuran or N , N -Dimethylformamide.

[0013] The molar ratio of the 1-aryl alkenyl borate to the alcohol compound is 1:2-1:4; the molar ratio of the 1-aryl alkenyl borate to oxalyl chloride is 1:5-1:6.

[0014] The metal ruthenium compound is any one of Ru(bpy)3Cl2 and Ru(bpy)3(BF4)2; the amount of the photocatalyst is 3 mol % of the molar amount of 1-aryl alkenyl borate.

[0015] The separation and purification is performed by filtering with a short silica gel column and then recrystallizing with ethanol to obtain the target product. A base is added during the reaction, and the base includes but is not limited to 2,6-lutidine, triethylamine, and 2,6-lutidine (the base is not necessary for the reaction, and the yield is slightly increased by adding the base).

[0016] The present invention provides β -Borate Esters- β -The application of chloroester compounds in the synthesis of pharmaceutical intermediates, β -Borate Esters- β Anhydrous tetrahydrofuran and 1,8-diazabicyclo[5.4.0]undec-7-ene are added to the chloroester compound in sequence, and the mixture is reacted at room temperature for 5 to 30 minutes under a nitrogen atmosphere. After the reaction is completed, the solvent is removed by distillation under reduced pressure, and the mixture is filtered through a silica gel short column to obtain the drug intermediate 3-pinacol borate-3-arylacrylate ethyl ester; The synthetic route is as follows: R 1 Any one selected from hydrogen, halogen, cyano, ester, sulfonyl, amide, alkoxy, alkyl with a carbon chain length of C1 to C10, and aryl; R 2 is an alkyl group with a carbon chain length of C1 to C8; R 3 The primary alkyl group, secondary alkyl group or tertiary alkyl group with a carbon chain length of C1 to C16, wherein the primary alkyl group includes methyl, ethyl, n-propyl, n-butyl, perfluorohexylethyl, and n-hexadecyl group, the secondary alkyl group includes isopropyl, cyclobutyl, cyclohexyl, cyclododecyl, and 2-adamantyl group, and the tertiary alkyl group includes 1-adamantyl group.

[0017] Drug molecules include 3-pinacol borate-3-phenyl ethyl acrylate, 3-pinacol borate-3 (4-methoxy-phenyl) ethyl acrylate, 3-pinacol borate-3-(4-trifluoromethyl-phenyl) ethyl acrylate, 3-pinacol borate-3-(3-bromo-phenyl) ethyl acrylate, 3-pinacol borate-3-(2-fluoro-phenyl) ethyl acrylate, 3-pinacol borate-3-(2-naphthyl) ethyl acrylate, 3-pinacol borate-3-phenyl butyl acrylate, 3-pinacol borate-3-phenyl cyclobutyl acrylate; β -Borate Esters- β The molar ratio of the chloroester compound to 1,8-diazabicyclo[5.4.0]undec-7-ene is 1:3 to 1:5.

[0018] Compared with the prior art, the present invention has the following advantages: 1. The present invention is a new synthesis method. β -Borate Esters- β -The most novel synthetic strategy for chloroester compounds; 2. The raw materials used in the present invention are cheap and easily available. Compared with the existing methods, the raw material processing is simple and the structure is diverse.

[0019] 3. Compared with the prior art, the reaction of the present invention utilizes light energy, has mild conditions, and is green and environmentally friendly.

[0020] 4. The method provided by the present invention has a wide range of substrate applications, and the obtained series of β -Borate Esters- β -Chloroester compounds can be quickly converted into drug molecules or active intermediates. DETAILED DESCRIPTION

[0021] The synthesis of the present invention is described below in conjunction with specific embodiments. β -Borate Esters- β -chloroesters are further described.

[0022] Example 1: Synthesis of ethyl 2-pinacol borate-2-chloro-3-phenylpropionate Oxalyl chloride (3.0 mmol) and anhydrous dichloromethane (3 mL) were added to a 25 mL reaction tube. A dichloromethane solution (3 mL) of ethanol (1.5 mmol) was added dropwise in an ice-water bath (0-5°C). The mixture was then reacted at room temperature for 30 min. The dichloromethane and excess oxalyl chloride were removed by concentration to obtain a light yellow liquid. 1-phenylvinylboronic acid pinacol ester (0.5 mmol) and tris(2,2'-bipyridyl)ruthenium dichloride (0.015 mol) were added and nitrogen was replaced three times. Anhydrous acetonitrile (5 mL) and additive 2,6-dimethylpyridine (0.75 mmol) were added in sequence under a nitrogen atmosphere. The reaction was then placed under two 30W blue light lamps (the reaction tube was about 2 cm away from the lamp bead, and the wavelength of the lamp bead was λ=460 ±10 nm) for 48 h. After the reaction was completed, the solvent was removed by vacuum distillation, and the target product was obtained as a light yellow solid by filtration with a silica gel short column and recrystallization with ethanol. The yield was 85%. The NMR data of the compound are as follows: 1 H NMR (600 MHz, Chloroform- d ) δ 7.58 (d, J = 7.6 Hz, 2H), 7.33 (dd, J = 7.8,7.8 Hz, 2H), 7.24 (dd,J = 7.2, 7.2 Hz, 1H), 4.17 (q, J = 7.2 Hz, 2H), 3.41 (d, J =16.5 Hz, 1H), 3.22 (d, J = 16.2 Hz, 1H), 1.27 (d, J = 4.2 Hz, 12H), 1.25 (t, J =7.2 Hz, 3H). 13 C NMR (151 MHz, Chloroform- d ) δ 170.97, 141.15, 128.39, 127.63,127.00, 85.08, 61.07, 46.47, 24.62, 24.57, 14.29. 11 B NMR (160 MHz, Chloroform- d ) δ 31.30. HRMS (ESI) calcd for C 17 H 25 BClO4(M+H) 339.1532, found 339.1526. Example 2: Synthesis of methyl 2-pinacol borate-2-chloro-3-phenylpropionate The synthesis method is the same as that of Example 1, wherein only the raw material ethanol is replaced by methanol, and the product is a white solid with a yield of 87%.

[0023] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.58 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 8.0, 7.5 Hz, 2H), 7.25 (dd, J =7.5, 7.0 Hz,1H), 3.71 (s, 3H), 3.43 (d, J = 16.5 Hz, 1H), 3.22 (d, J = 16.5 Hz, 1H), 1.28 (s, 6H), 1.27 (s, 6H). 13 C NMR (126 MHz, Chloroform- d) δ 171.40, 141.08, 128.47,127.71, 126.99, 85.17, 52.11, 46.33, 24.61, 24.59. 11 B NMR (160 MHz, Chloroform- d ) δ 31.09. HRMS (ESI) calcd for C 16 H 22 BClNaO4(M+Na) 347.1195, found347.1202. Example 3: Synthesis of 2-Pinacol Borate-2-Chloro-3-Phenylpropionic Acid Propyl Ester The synthesis method is the same as that of Example 1, wherein only the raw material ethanol is replaced with n-propanol, and the product is a white solid with a yield of 85%.

[0024] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.58 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 8.0, 7.5 Hz, 2H), 7.25 (dd, J = 7.0, 7.0Hz, 1H), 4.10 – 4.05 (m, 2H), 3.42(d, J = 16.5 Hz, 1H), 3.23 (d, J = 16.5 Hz,1H), 1.68 – 1.62 (m, 2H), 1.274 (s, 6H),1.268 (s, 6H), 0.92 (t, J = 7.5 Hz,3H). 13 C NMR (126 MHz, Chloroform- d ) δ 171.13, 141.19, 128.43, 127.66, 127.04, 85.11, 66.70, 46.44, 24.65, 24.60, 22.08, 10.45. 11 B NMR (160 MHz, Chloroform- d ) δ 31.37. HRMS (ESI) calcd for C 18 H 26BClNaO4(M+Na) 375.1508, found 375.1518. Example 4: Synthesis of 2-Pinacol Borate-2-Chloro-3-Phenylpropionic Acid n-Butyl Ester The synthesis method is the same as that of Example 1, wherein only the raw material ethanol is replaced with n-butanol. The product is a white solid with a yield of 80%.

[0025] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.58 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 8.0, 7.5 Hz, 2H), 7.24 (dd, J = 7.5, 7.0Hz, 1H), 4.12 (td, J = 6.5, 2.0 Hz, 2H), 3.41 (d, J = 16.5 Hz, 1H), 3.22 (d, J =16.5 Hz, 1H), 1.63 – 1.57 (m, 2H), 1.39 – 1.31 (m, 2H), 1.28 (s, 6H), 1.27(s, 6H),0.91 (t, J = 7.5 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d ) δ 171.13,141.18, 128.42, 127.65, 127.04, 85.11, 64.98, 46.45, 30.74, 24.64,24.59,19.17, 13.80. 11 B NMR (160 MHz, Chloroform- d ) δ 31.23. HRMS (ESI) calcd forC 19 H 28 BClNaO4(M+Na) 389.1665, found 389.1671. Example 5: Synthesis of 2-pinacol borate-2-chloro-3-phenylpropionic acid hexadecyl ester The synthesis method is the same as that of Example 1, wherein only the raw material ethanol is replaced with hexadecanol. The product is a white solid with a yield of 65%.

[0026] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.58 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 8.0, 7.5 Hz, 2H), 7.24 (dd, J = 7.5, 7.0Hz, 1H), 4.13 – 4.08 (m, 2H), 3.41 (d, J = 16.5 Hz, 1H), 3.22 (d, J = 16.5 Hz,1H), 1.63 – 1.58 (m, 2H), 1.31 – 1.30 (m, 4H), 1.28 (s, 6H), 1.27 (s, 6H),1.26 – 1.23 (m, 22H),0.88 (t, J = 7.5 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d ) δ171.15, 141.21, 128.43, 127.66, 127.06, 85.11, 65.32, 46.47, 32.07, 29.84,29.82, 29.80, 29.72, 29.64, 29.51, 29.37, 28.72, 25.97, 24.66, 24.61, 22.84,14.26. 11 B NMR (160 MHz, Chloroform- d ) δ 32.06. Example 6: Synthesis of 2-Pinacol Borate-2-Chloro-3-Phenylpropionic Acid Isopropyl Ester The synthesis method is the same as that of Example 1, wherein only the raw material ethanol is replaced with isopropanol. The product is a white solid with a yield of 78%.

[0027] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.50 (d, J= 8.0 Hz, 2H), 7.24 (dd, J = 7.5, 7.5 Hz, 2H), 7.16 (dd, J = 7.5, 7.0Hz, 1H), 5.00 – 4.93 (m, 1H), 3.30 (d, J = 16.5 Hz, 1H), 3.12 (d, J = 16.5 Hz,1H), 1.20 (s, 6H), 1.19 (s, 6H),1.16 (d, J = 6.0 Hz, 3H), 1.13 (d, J = 6.5 Hz,3H). 13 C NMR (126 MHz, Chloroform- d ) δ 170.58, 141.22, 128.35, 127.59, 127.04,85.02, 68.62, 46.66,24.65, 24.56, 21.90, 21.83. 11 B NMR (160 MHz, Chloroform- d )δ 31.14. HRMS (ESI) calcd for C 18 H 26 BClNaO4(M+Na) 375.1508, found 375.1513. Example 7: Synthesis of 2-Pinacol borate-2-chloro-3-phenylpropionic acid cyclohexyl ester The synthesis method is the same as that of Example 1, wherein only the raw material ethanol is replaced by cyclohexanol, and the product is a white solid with a yield of 83%.

[0028] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.58 (d, J = 7.5 Hz, 2H), 7.32 (dd, J = 7.5, 7.5 Hz, 2H), 7.26 – 7.22 (m, 1H), 4.80 (tt, J = 9.0, 3.5 Hz, 1H), 3.40 (d, J = 16.5 Hz, 1H), 3.21 (d, J= 16.5 Hz,1H), 1.87 – 1.79 (m, 2H), 1.73 – 1.67 (m, 2H), 1.52 (dt, J = 13.0, 4.4 Hz,1H), 1.44 – 1.32 (m,5H), 1.27 (d, J = 3.0 Hz, 12H). 13 C NMR (126 MHz, Chloroform-d) δ 170.57, 141.29, 128.38, 127.61, 127.10, 85.06, 46.71, 31.71,31.65,25.47, 24.70, 24.62, 23.86, 23.83. 11 B NMR (160 MHz, Chloroform- d ) δ 31.22.HRMS (ESI) calcd for C 21 H 30 BClNaO4(M+Na) 415.1822, found 415.1822. Example 8: Synthesis of 2-Pinacol Borate-2-Chloro-3-Phenylpropionic Acid Cyclobutyl Ester The synthesis method is the same as that of Example 1, wherein only the raw material ethanol is replaced by cyclobutanol, and the product is a white solid with a yield of 82%.

[0029] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.59 – 7.56 (m, 2H), 7.35 – 7.31 (m, 2H), 7.27 – 7.23 (m, 1H), 5.04 – 4.97(m,1H), 3.39 (d, J = 16.5 Hz, 1H), 3.20 (d, J = 16.5 Hz, 1H), 2.37 – 2.30 (m, 2H), 2.12 – 2.00 (m, 2H), 1.82 – 1.74 (m, 1H), 1.65 – 1.55 (m, 1H), 1.27 (s, 12H). 13 C NMR (126 MHz, Chloroform- d) δ 170.32, 141.19, 128.40, 127.64, 127.06,85.08, 69.54, 46.40, 30.38, 30.34, 24.66,24.57, 13.68. 11 B NMR (128 MHz, Chloroform- d ) δ 31.30.HRMS (ESI) calcd for C 21 H 30 BClNaO4(M+Na) 415.1822, found415.1822. Example 9: Synthesis of 2-pinacol borate-2-chloro-3-phenylpropionic acid (2-adamantane) ester The synthesis method is the same as that of Example 1, wherein only the raw material ethanol is replaced with 2-adamantanol. The product is a white solid with a yield of 77%.

[0030] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.61 – 7.59 (m, 2H), 7.32 (dd, J = 8.0, 7.5 Hz, 2H), 7.26 – 7.22 (m, 1H), 4.95(d, J = 3.5, 3.0 Hz, 1H), 3.43 (d, J = 16.5 Hz, 1H), 3.28 (d, J = 16.5 Hz, 1H), 2.03 – 1.93 (m, 4H), 1.85 – 1.80 (m, 4H), 1.77 – 1.72 (m, 4H), 1.54 – 1.49 (m, 2H), 1.28 (s, 6H), 1.27 (s, 6H). 13 C NMR (126 MHz, Chloroform- d ) δ 170.61,141.30, 128.38, 127.59, 127.09, 85.06, 77.97, 46.73, 37.51, 36.45, 36.39,31.89, 31.86, 31.81, 31.78, 27.30, 27.10,24.68, 24.61. 11B NMR (160 MHz, Chloroform- d ) δ 31.54. HRMS (ESI) calcd for C 25 H 34 BClNaO4(M+Na) 467.2135, found467.2136. Example 10: Synthesis of 2-pinacol borate-2-chloro-3-phenylpropionic acid (1-adamantane) ester The synthesis method is the same as that of Example 1, wherein only the raw material ethanol is replaced with 1-adamantanol. The product is a white solid with a yield of 75%.

[0031] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.58 – 7.56 (m, 2H), 7.32 (dd, J = 8.0, 7.5 Hz, 2H), 7.25 – 7.22 (m, 1H), 3.35(d, J = 17.0 Hz, 1H), 3.16 (d, J = 16.5 Hz, 1H), 2.14 (s, 3H), 2.10 (s, 6H), 1.65(s, 6H), 1.273 (s, 6H), 1.269 (s, 6H). 13 C NMR (126 MHz, Chloroform- d ) δ170.17, 141.45, 128.33, 127.51, 127.16, 84.95, 81.66, 47.35, 41.38, 36.28,30.97, 24.77, 24.59. 11 B NMR (160 MHz, Chloroform- d ) δ 31.31. HRMS (ESI) calcdfor C 25 H 34 BClNaO4(M+Na) 467.2135, found 467.2142. Example 11: Synthesis of ethyl 2-pinacol borate-2-chloro-3-(4-tert-butyl-phenyl) propionate The synthesis method is the same as that of Example 1, wherein only the raw material 1-phenylvinylboronic acid pinacol ester is replaced with 1-(4-tert-butylphenyl)vinylboronic acid pinacol ester. The product is a white solid with a yield of 86%.

[0032] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (600 MHz, Chloroform- d ) δ7.49 (d, J = 8.4 Hz, 2H), 7.34 (d, J = 9.0 Hz, 2H), 4.17 (q, J = 7.2 Hz, 2H), 3.39(d, J = 16.8 Hz, 1H), 3.23 (d, J = 16.8 Hz, 1H), 1.30 (s, 9H), 1.29 (s, 6H), 1.28(s, 6H), 1.24 (t, J = 7.2 Hz, 3H). 13 C NMR (151 MHz, Chloroform- d ) δ 171.03,150.52, 138.13, 126.70, 125.34, 85.02, 61.00, 46.42, 34.55, 31.37, 24.68,24.62, 14.29. 11 B NMR (160 MHz, Chloroform- d ) δ 30.96. HRMS (ESI) calcd forC 21 H 32 BClNaO4(M+Na) 417.1978, found 417.1977. Example 12: Synthesis of ethyl 2-pinacol borate-2-chloro-3-(4-chloro-phenyl) propionate The synthesis method is the same as that of Example 1, wherein only the raw material 1-phenylvinylboronic acid pinacol ester is replaced with 1-(4-chlorophenyl)vinylboronic acid pinacol ester. The product is a white solid with a yield of 77%.

[0033] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (600 MHz, Chloroform- d ) δ7.53 (d, J= 8.4 Hz, 2H), 7.29 (d, J = 8.4 Hz, 2H), 4.16 (qd, J = 7.2, 3.0 Hz, 2H),3.34 (d, J = 16.8 Hz, 1H), 3.20 (d, J = 16.8 Hz, 1H), 1.27 (s, 6H), 1.26 (s, 6H), 1.23 (t, J = 7.2 Hz, 3H). 13 C NMR (151 MHz, Chloroform- d ) δ 170.72, 139.81,133.51, 128.59, 128.46, 85.18, 61.15, 46.54, 24.58, 24.54, 14.25. 11 B NMR (160MHz, Chloroform- d ) δ 30.95. HRMS(ESI) calcd for C 17 H 23 BCl2NaO4(M+Na) 395.0962, found 395.0959. Example 13: Synthesis of 2-Pinacol Borate-2-Chloro-3-(4-trifluoromethyl-phenyl) Ethyl Propionate The synthesis method is the same as that of Example 1, wherein only the raw material 1-phenylvinylboronic acid pinacol ester is replaced with 1-(4-trifluoromethylphenyl)vinylboronic acid pinacol ester. The product is a white solid with a yield of 77%.

[0034] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.73 (d, J = 8.5 Hz, 2H), 7.59 (d, J = 8.5 Hz, 2H), 4.16 (qd, J = 7.0, 2.5 Hz, 2H),3.38 (d, J = 16.5 Hz, 1H), 3.23 (d, J = 16.5 Hz, 1H), 1.28 (s, 6H), 1.27 (s, 6H), 1.24 (t,J = 7.0 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d ) δ 170.69, 145.31,129.76 (q, J = 32.9 Hz), 127.66, 125.32 (q, J = 3.5 Hz),124.13 (q, J = 272.3 Hz),85.35, 61.28, 46.64, 24.60, 24.56, 14.26. 11 B NMR (160 MHz, Chloroform- d ) δ30.92. 19 F NMR (470 MHz, Chloroform- d ) δ -62.65. HRMS (ESI) calcd forC 18 H 24 BClF3O4(M+H) 407.1406, found 407.1406. Example 14: Synthesis of ethyl 2-pinacol borate-2-chloro-3-(3-fluoro-phenyl) propionate The synthesis method is the same as that of Example 1, wherein only the raw material 1-phenylvinylboronic acid pinacol ester is replaced with 1-(3-fluorophenyl)vinylboronic acid pinacol ester. The product is a white solid with a yield of 83%.

[0035] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.37 – 7.33 (m, 2H), 7.31 – 7.26 (m, 1H), 6.96 – 6.92 (m, 1H), 4.17 (q, J = 7.0Hz, 2H), 3.36 (d, J = 16.5 Hz, 1H), 3.20 (d, J = 16.5 Hz, 1H), 1.280 (s, 6H), 1.275 (s, 6H), 1.24 (t, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d) δ170.64, 162.59 (d, J = 246.0 Hz), 143.75 (d, J = 7.3 Hz), 129.74 (d, J = 8.3 Hz),122.62 (d, J = 2.9 Hz), 114.55 (d, J = 1.4 Hz),114.38 (d, J = 4.3 Hz), 85.15, 61.08, 46.51, 24.50, 24.46, 14.17. 11 B NMR (160 MHz, Chloroform- d ) δ 31.16 19 FNMR (470 MHz, Chloroform- d ) δ -112.63. HRMS (ESI) calcd for C 17 H 23 BClFNaO4(M+Na) 379.1257, found 379.1262. Example 15: Synthesis of ethyl 2-pinacol borate-2-chloro-3-(3-bromo-phenyl)propionate The synthesis method is the same as that of Example 1, wherein only the raw material 1-phenylvinylboronic acid pinacol ester is replaced with 1-(3-bromophenyl)vinylboronic acid pinacol ester. The product is a white solid with a yield of 74%.

[0036] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.74 (s, 1H), 7.51 (d, J = 7.5 Hz, 1H), 7.37 (d, J = 7.5 Hz, 1H), 7.19 (dd, J =8.0, 7.5 Hz, 1H), 4.16 (q, J = 7.0 Hz, 2H), 3.34 (d, J = 16.5 Hz, 1H), 3.18 (d, J =16.5 Hz, 1H), 1.27 (s, 12H), 1.23 (d, J= 7.5 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d ) δ 170.71, 143.48, 130.73, 130.28, 129.87, 125.81, 122.48,85.27, 61.21, 46.48, 24.58, 24.53, 14.26. 11 B NMR (160 MHz, Chloroform- d ) δ31.26. HRMS(ESI) calcd for C 17 H 24 BBrClO4(M+H) 417.0637, found 417.0625. Example 16: Synthesis of ethyl 2-pinacol borate-2-chloro-3-(2-fluoro-phenyl) propionate The synthesis method is the same as that of Example 1, wherein only the raw material 1-phenylvinylboronic acid pinacol ester is replaced with 1-(2-fluorophenyl)vinylboronic acid pinacol ester. The product is a white solid with a yield of 81%.

[0037] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.69 (ddd, J = 8.0, 8.0, 1.5 Hz, 1H), 7.28 – 7.24 (m, 1H), 7.14 (ddd, J = 9.0,7.5, 1.0 Hz, 1H), 7.01 (ddd, J = 8.5, 8.0, 1.0 Hz, 1H), 4.05 (q, J = 7.0 Hz, 2H),3.34 (d, J = 16.0 Hz, 1H), 3.29 (d, J = 16.0 Hz, 1H), 1.30 (s, 12H), 1.14 (t, J =7.0 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d ) δ 170.08, 159.80 (d, J = 246.8 Hz),129.51 (d,J = 11.3 Hz), 129.49, 128.42 (d, J = 11.7 Hz), 124.14 (d, J = 3.4 Hz),115.47 (d, J = 22.6 Hz), 85.09, 60.69, 44.45, 44.43, 24.60, 14.18. 11 B NMR (160MHz, Chloroform- d ) δ 30.71; 19 F NMR (470 MHz, Chloroform- d ) δ -111.01. HRMS(ESI) calcd for C 17 H 23 BClFNaO4(M+Na) 379.1257, found 379.1262. Example 17: Synthesis of ethyl 2-pinacol borate-2-chloro-3-(4'-phenyl-phenyl) propionate The synthesis method is the same as that of Example 1, wherein only the raw material 1-phenylvinylboronic acid pinacol ester is replaced with 1-(4'-phenylphenyl)vinylboronic acid pinacol ester. The product is a white solid with a yield of 86%.

[0038] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.67 (d, J = 8.5 Hz, 2H), 7.61 – 7.59 (m, 2H), 7.58 (d, J = 8.5 Hz, 2H), 7.44(dd, J = 8.0, 7.5 Hz, 2H), 7.36 – 7.33 (m, 1H), 4.20 (q, J = 7.0 Hz, 2H), 3.46(d, J = 16.5 Hz, 1H), 3.28 (d, J = 16.5 Hz, 1H), 1.31 (s, 6H), 1.30 (s, 6H), 1.27(t, J = 7.0 Hz, 3H). 13C NMR (126 MHz, Chloroform- d ) δ 171.01, 140.60, 140.45,140.26, 128.90, 127.54, 127.52, 127.17, 127.10, 85.17, 61.15, 46.45, 24.68,24.62, 14.32. 11 B NMR (160 MHz, Chloroform- d ) δ 31.14. HRMS(ESI) calcd forC 23 H 28 BClNaO4(M+Na) 437.1665, found 437.1655. Example 18: Synthesis of ethyl 2-pinacol borate-2-chloro-3-(2-naphthyl)propionate The synthesis method is the same as that of Example 1, wherein only the raw material 1-phenylvinylboronic acid pinacol ester is replaced with 1-naphthylvinylboronic acid pinacol ester, and the product is a white solid with a yield of 82%.

[0039] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ8.00 (s, 1H), 7.84 – 7.81 (m,3H), 7.76 (d, J = 8.5 Hz, 1H), 7.49 – 7.47 (m,2H), 4.22 (q, J = 7.0 Hz, 2H), 3.59 (d, J = 16.5 Hz, 1H), 3.35 (d, J = 16.5 Hz,1H), 1.31 (s, 6H), 1.29 (s, 6H), 1.27 (d, J = 7.5 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d ) δ 171.02, 138.52, 133.11, 132.68, 128.40, 128.10, 127.52,126.40, 126.31, 125.63, 125.27, 85.18,61.13, 46.18, 24.66, 24.57, 14.29.11 BNMR (160 MHz, Chloroform- d ) δ 31.67. HRMS(ESI) calcd for C 21 H 26 BClNaO4(M+Na)411.1509, found 411.1518. Example 19: Synthesis of 2-neopentyl glycol borate-2-chloro-3-phenylpropionic acid ethyl ester The synthesis method is the same as that of Example 1, wherein only the raw material 1-phenylvinylboronic acid pinacol ester is replaced with 1-phenylvinyl neopentyl glycol borate, and the product is a white solid with a yield of 70%.

[0040] The NMR data and high-resolution data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ7.54 (d, J = 7.5 Hz, 2H), 7.33 (dd, J = 8.0, 7.5 Hz, 2H), 7.24 (dd, J = 7.5, 7.0Hz, 1H), 4.25 – 4.16 (m, 2H), 3.69 (s, 4H), 3.46 (d, J = 16.0 Hz, 1H), 3.18 (d, J = 16.5 Hz, 1H), 1.28 (t, J = 7.0 Hz, 3H), 0.92 (s, 6H). 13 C NMR (126 MHz, Chloroform- d ) δ 171.85, 142.05, 128.43, 127.45, 126.85, 72.75, 61.15, 46.21,31.88, 22.03, 14.31. 11 B NMR (160 MHz, Chloroform- d ) δ 27.73; HRMS(ESI) calcdfor C 16 H 22 BClNaO4(M+Na) 347.1195, found 347.1204. β -Borate Esters- β-Application of chloroester compounds: Synthesis of 3-pinacol borate-3-aryl acrylate ethyl ester Example 20: Synthesis of 3-Pinacol Borate-3-Phenyl Acrylic Acid Ethyl Ester Add 2-pinacol borate-2-chloro-3-phenylpropionic acid ethyl ester (1.0 mmol) to a 25 mL reaction tube, add anhydrous tetrahydrofuran (10 mL) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (4.0 mmol) in sequence under a nitrogen atmosphere, and react at room temperature. Then use TLC to monitor the reaction progress. After the reaction is completed, the solvent is removed by distillation under reduced pressure, and the target product is obtained by filtration on a silica gel short column as a light yellow oil with a yield of 80%. The NMR data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ 7.51 – 7.49 (m, 2H), 7.37 – 7.33 (m, 3H), 6.44 (s,1H), 4.26 (q, J = 7.0 Hz, 2H), 1.42 (s, 12H), 1.31 (t, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d ) δ 168.17, 138.76, 129.16, 128.80, 127.24, 126.18,84.44, 60.87, 25.17, 14.39.11B NMR (160 MHz, Chloroform-d) δ 31.00. Example 21: Synthesis of ethyl 3-pinacol borate-3 (4-methoxy-phenyl) acrylate Add 2-pinacol borate-2-chloro-3-(4-methoxy-phenyl)propionic acid ethyl ester (1.0 mmol) to a 25 mL reaction tube, and add anhydrous tetrahydrofuran (10 mL) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (4.0 mmol) in sequence under a nitrogen atmosphere. Then use TLC to monitor the reaction progress. After the reaction is completed, the solvent is removed by distillation under reduced pressure, and the target product is obtained by filtration on a silica gel short column as a light yellow oil with a yield of 70%. The NMR data of the compound are as follows: 1 H NMR (500MHz, Chloroform- d ) δ 7.45 (d, J= 9.0 Hz, 2H), 6.88 (d, J = 9.0 Hz, 2H), 6.38 (s,1H), 4.24 (q, J = 7.0 Hz, 2H), 3.81 (s, 3H), 1.42 (s, 12H), 1.30 (t, J = 7.0 Hz,3H). Example 22: Synthesis of ethyl 3-pinacol borate-3-(4-trifluoromethyl-phenyl)acrylate Add 2-pinacol borate-2-chloro-3-(4-trifluoromethyl-phenyl)propionic acid ethyl ester (1.0 mmol) to a 25 mL reaction tube, and add anhydrous tetrahydrofuran (10 mL) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (4.0 mmol) in sequence under a nitrogen atmosphere. Then use TLC to monitor the reaction progress. After the reaction is completed, the solvent is removed by distillation under reduced pressure, and the target product is obtained as a light yellow oil by filtration on a silica gel short column with a yield of 76%. The NMR data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ 7.61 (d, J = 8.0 Hz, 2H), 7.58 (d, J = 8.5 Hz, 2H), 6.45 (s, 1H), 4.27 (q, J = 7.0 Hz, 2H), 1.41 (s, 12H), 1.31 (t, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d ) δ 167.78, 142.79, 142.41, 130.87 (q, J = 32.4Hz), 128.31, 127.49, 125.79 (q, J = 4.0 Hz),124.15 (q, J = 272.7 Hz), 84.68, 61.20, 25.11, 14.34. 11 B NMR (160 MHz, Chloroform- d ) δ 31.03. Example 23: Synthesis of ethyl 3-pinacol borate-3-(3-bromo-phenyl)acrylate Add 2-pinacol borate-2-chloro-3-(3-bromo-phenyl)propionic acid ethyl ester (1.0 mmol) to a 25 mL reaction tube, and add anhydrous tetrahydrofuran (10 mL) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (4.0 mmol) in sequence under a nitrogen atmosphere. Then use TLC to monitor the reaction progress. After the reaction is completed, the solvent is removed by distillation under reduced pressure, and the target product is obtained by filtration on a silica gel short column as a light yellow oil with a yield of 70%. The NMR data of the compound are as follows: 1 H NMR (500MHz, Chloroform- d ) δ 7.56 (dd, J = 2.0, 1.5 Hz, 1H), 7.38 – 7.36 (m, 1H), 7.34 –7.32 (m, 1H), 7.14 (dd, J = 8.0, 8.0 Hz, 1H), 6.34 (s, 1H), 4.18 (q, J = 7.0 Hz,2H), 1.33 (s, 12H), 1.23 ( t , J = 7.0 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d ) δ167.86, 140.78, 131.97, 130.29, 130.25, 127.27, 125.76,122.98, 84.59, 61.07,25.11, 14.35. 11 B NMR (160 MHz, Chloroform- d ) δ 30.67. Example 24: Synthesis of ethyl 3-pinacol borate-3-(2-fluoro-phenyl)acrylate Add 2-pinacol borate-2-chloro-3-(2-fluoro-phenyl)propionic acid ethyl ester (1.0 mmol) to a 25 mL reaction tube, and add anhydrous tetrahydrofuran (10 mL) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (4.0 mmol) in sequence under a nitrogen atmosphere. Then use TLC to monitor the reaction progress. After the reaction is completed, the solvent is removed by distillation under reduced pressure, and the target product is obtained by filtration on a silica gel short column as a light yellow oil with a yield of 78%. The NMR data of the compound are as follows: 1H NMR (500MHz, Chloroform- d ) δ 7.45 (ddd, J = 8.0, 7.5, 12.0 Hz, 1H), 7.31 – 7.26 (m,1H), 7.11 (ddd, J = 7.5, 7.5, 1.0 Hz, 1H), 7.06 (ddd, J = 8.5, 8.5, 1.0 Hz, 1H), 6.57 (s, 1H), 4.25 (q, J = 7.0 Hz, 2H), 1.39 (s, 12H), 1.30 (t, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d ) δ 167.83, 160.51 (d, J = 251.4 Hz), 130.61 (d, J =8.7 Hz), 129.81 (d, J = 3.2 Hz), 129.39 (d, J = 5.4 Hz), 126.7 (d, J = 13.1 Hz),124.4 (d, J = 3.3 Hz), 116.2 (d, J = 22.7 Hz),84.41, 60.97, 25.20, 14.36. 11 B NMR (160 MHz, Chloroform- d ) δ 30.36. Example 25: Synthesis of 3-pinacol borate-3-(2-naphthyl)ethyl acrylate Add 2-pinacol borate-2-chloro-3-(2-naphthyl)propionic acid ethyl ester (1.0 mmol) to a 25 mL reaction tube, and add anhydrous tetrahydrofuran (10 mL) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (4.0 mmol) in sequence under a nitrogen atmosphere. Then use TLC to monitor the reaction progress. After the reaction is completed, the solvent is removed by distillation under reduced pressure, and the target product is obtained as a light yellow oil by filtration on a silica gel short column with a yield of 70%. The NMR data of the compound are as follows: 1 H NMR (500 MHz, Chloroform-d ) δ 7.88 (d, J = 1.0 Hz, 1H),7.74 – 7.70 (m, 4H), 7.53 (dd, J = 8.5,2.0 Hz, 1H), 7.38 (dd, J = 6.5, 3.5 Hz, 2H), 6.49 (s, 1H), 4.19 (q, J = 7.0 Hz,2H), 1.36 (s, 12H), 1.23 (t, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, Chloroform- d ) δ168.25, 136.11, 133.67, 133.41, 128.57, 128.53, 127.74, 127.62, 126.77,126.50, 126.25, 124.41, 84.51, 60.91, 25.22, 14.40. 11 B NMR (160 MHz, Chloroform- d ) δ 30.65. Example 26: Synthesis of 3-Pinacol Borate-3-Phenyl Acrylic Acid Butyl Ester Add 2-pinacol borate-2-chloro-3-phenylpropionic acid butyl ester (1.0 mmol) to a 25 mL reaction tube, and add anhydrous tetrahydrofuran (10 mL) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (4.0 mmol) in sequence under a nitrogen atmosphere. Then use TLC to monitor the reaction progress. After the reaction is completed, the solvent is removed by distillation under reduced pressure, and the target product is obtained by filtration on a silica gel short column as a light yellow oil with a yield of 84%. The NMR data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ 7.51 – 7.49 (m, 2H), 7.37 – 7.33 (m, 3H), 6.45 (s, 1H), 4.20(t, J = 6.5 Hz, 2H), 1.69– 1.64 (m, 2H), 1.45– 1.39(m, 14H), 0.95 (t, J = 7.5 Hz,3H). 13C NMR (126 MHz, Chloroform- d ) δ 168.29, 138.74, 129.14, 128.77, 127.22,126.14, 84.40, 64.80, 30.79, 25.16, 19.23, 13.81. 11 B NMR (160 MHz, Chloroform- d ) δ 30.80 Example 27: Synthesis of 3-Pinacol borate-3-phenylacrylate cyclobutyl ester 2-Pinacol borate-2-chloro-3-phenylpropionic acid cyclobutyl ester (1.0 mmol) was added to a 25 mL reaction tube, and anhydrous tetrahydrofuran (10 mL) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (4.0 mmol) were added in sequence under a nitrogen atmosphere. The reaction progress was then monitored by TLC. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the target product was obtained by filtration on a silica gel short column as a light yellow oil with a yield of 87%. The NMR data of the compound are as follows: 1 H NMR (500 MHz, Chloroform- d ) δ 7.50 – 7.49 (m, 2H), 7.37 – 7.33 (m, 3H), 6.42 (s, 1H), 5.14(p, J = 7.5 Hz, 1H), 2.40 – 2.34 (m, 2H), 2.17 – 2.09 (m, 2H), 1.84 – 1.76 (m,1H), 1.66 – 1.57 (m, 1H), 1.41 (s, 12H). 13 C NMR (126 MHz, Chloroform- d ) δ167.44, 138.74, 129.13, 128.77, 127.21, 126.14, 84.38, 68.95, 30.55, 25.14,13.58. 11 B NMR (160 MHz, Chloroform- d ) δ 30.55.

Claims

1. A β -Borate Esters- β - A method for synthesizing chloroester compounds, characterized in that: Using 1-aryl alkenyl borate, alcohol compound and oxalyl chloride as raw materials, metal ruthenium compound as photocatalyst, adding additives, reacting in an organic solvent under N2 atmosphere, under visible light at room temperature for 40 to 50 hours, removing the solvent by vacuum distillation, and separating and purifying to obtain the target product; β -Borate Esters- β -Chloroester compounds have the structural formula: Where: R 1 is selected from any one of hydrogen, halogen, cyano, ester, sulfonyl, amide, alkoxy, alkyl with a carbon chain length of C1 to C10, and aryl; R 2 is an alkyl group with a carbon chain length of C1 to C8; R 3 Selected from alkyl groups with carbon chain lengths of C1 to C16.

2. The method according to claim 1 β -Borate Esters- β - A method for synthesizing chloroester compounds, characterized in that: β -Borate Esters- β -Chloroester compounds have R 3 It is a primary alkyl group, a secondary alkyl group or a tertiary alkyl group, wherein the primary alkyl group includes methyl, ethyl, n-propyl, n-butyl, perfluorohexylethyl, and n-hexadecyl group, the secondary alkyl group includes isopropyl, cyclobutyl, cyclohexyl, cyclododecyl, and 2-adamantyl group, and the tertiary alkyl group includes 1-adamantyl group.

3. The method according to claim 1 β -Boric acid ester - β - A method for synthesizing chloroester compounds, characterized in that: The structural formula of 1-aryl alkenyl borate is: Among them, R 1 is selected from any one of hydrogen, halogen, cyano, ester, sulfonyl, amide, alkoxy, alkyl with a carbon chain length of C1 to C10, and aryl; R 2 It is an alkyl group with a carbon chain length of C1~C8.

4. The method according to claim 1 β -Borate Esters- β - A method for synthesizing chloroester compounds, characterized in that: The molar ratio of the 1-aryl alkenyl borate to the alcohol compound is 1:2-1:4; the molar ratio of the 1-aryl alkenyl borate to oxalyl chloride is 1:5-1:

6.

5. The method according to claim 1 β -Borate Esters- β - A method for synthesizing chloroester compounds, characterized in that: The alcohol compound is a primary alcohol, a secondary alcohol or a tertiary alcohol.

6. The method according to claim 4 β -Borate Esters- β - A method for synthesizing chloroester compounds, characterized in that: The primary alcohols include methanol, ethanol, propanol, and butanol; the secondary alcohols include isopropanol, cyclohexanol, and menthol; and the tertiary alcohols include 1-adamantanol and tert-butanol.

7. The method according to claim 1 β -Borate Esters- β - A method for synthesizing chloroester compounds, characterized in that: The metal ruthenium compound is any one of Ru(bpy)3Cl2 and Ru(bpy)3(BF4)2; the amount of the photocatalyst is 3 mol % of the molar amount of 1-aryl alkenyl borate; the additive is any one of alkyl tertiary amine, aromatic tertiary amine, thiol, thiophenol, and Hans ester; the amount of the additive is 1.5 times the molar amount of 1-aryl alkenyl borate.

8. The method according to claim 1 β -Borate Esters- β - A method for synthesizing chloroester compounds, characterized in that: The organic solvent is acetonitrile, dichloromethane, 1,2-dichloroethane, 1,4-dioxane, tetrahydrofuran or N , N -dimethylformamide; the visible light is a 25~35W blue light lamp.

9. The method of claim 1 β -Borate Esters- β -Application of chloroester compounds in the synthesis of drug intermediates, characterized by: exist β -Borate Esters- β Anhydrous tetrahydrofuran and 1,8-diazabicyclo[5.4.0]undec-7-ene are added to the chloroester compound in sequence, and the mixture is reacted at room temperature for 5 to 30 minutes under a nitrogen atmosphere. After the reaction is completed, the solvent is removed by distillation under reduced pressure, and the mixture is filtered through a silica gel short column to obtain the drug intermediate 3-pinacol borate-3-arylacrylate ethyl ester; The structural formula of the drug molecule is: R 1 Any one selected from hydrogen, halogen, cyano, ester, sulfonyl, amide, alkoxy, alkyl with a carbon chain length of C1 to C10, and aryl; R 2 is an alkyl group with a carbon chain length of C1 to C8; R 3 The primary alkyl group, secondary alkyl group or tertiary alkyl group with a carbon chain length of C1 to C16, wherein the primary alkyl group includes methyl, ethyl, n-propyl, n-butyl, perfluorohexylethyl, and n-hexadecyl group, the secondary alkyl group includes isopropyl, cyclobutyl, cyclohexyl, cyclododecyl, and 2-adamantyl group, and the tertiary alkyl group includes 1-adamantyl group.

10. The method according to claim 9 β -Borate Esters- β -The application of chloroester compounds in the synthesis of drug molecules is characterized by: Drug intermediates include 3-pinacol borate-3-phenyl ethyl acrylate, 3-pinacol borate-3 (4-methoxy-phenyl) ethyl acrylate, 3-pinacol borate-3-(4-trifluoromethyl-phenyl) ethyl acrylate, 3-pinacol borate-3-(3-bromo-phenyl) ethyl acrylate, 3-pinacol borate-3-(2-fluoro-phenyl) ethyl acrylate, 3-pinacol borate-3-(2-naphthyl) ethyl acrylate, 3-pinacol borate-3-phenyl butyl acrylate, 3-pinacol borate-3-phenyl cyclobutyl acrylate; β -Borate Esters- β The molar ratio of the chloroester compound to 1,8-diazabicyclo[5.4.0]undec-7-ene is 1:3 to 1:5.

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