A process for the preparation of 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Abstract

The present application relates to chemical synthesis technical field, and disclose a kind of 2-(4-(tert-butyl) naphthalene-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborinane preparation method, comprising the following steps: 1), formula (I) compound and formula (II) compound occur Blyss reaction, obtain formula (III) compound;2), formula (III) compound is condensed reaction, obtain formula (IV) compound;3), formula (IV) compound occurs bromination, obtain formula (V) compound;4), formula (V) compound and formula (VI) compound are reacted, obtain formula (VII) compound;5), formula (VII) compound and formula (VIII) compound occur Grignard exchange reaction, obtain formula (IX) compound.The method for adopting in the present application, raw material is cheap and easy to obtain, does not use expensive palladium catalyst, can significantly reduce cost.

Description

Technical Field

[0001] This invention relates to the field of chemical synthesis technology, specifically to a method for preparing 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are self-emissive display technologies without backlights or liquid crystals, boasting advantages such as high brightness, high resolution, wide viewing angles (over 170°), flexibility, fast response speed, thinness, light weight, and low power consumption. Therefore, OLEDs are attracting increasing attention for their applications in flat panel displays, lighting, and backlighting. As a novel display technology, the industrialization of OLEDs still faces many key challenges, with research on OLED molecular materials being a key trend for future development. 2-(4-(tert-butyl)naphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane is a key intermediate in the synthesis of red light doping materials for OLEDs and has received widespread attention and research in recent years.

[0003] According to US2018 / 0097187, the synthesis of 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane mainly uses 6-tert-butyl-4-hydroxy-2H-pyran-2-one, phosphorus tribromide, anthranilic acid, and dipinacol boronic acid ester as raw materials, and proceeds through a three-step reaction involving chlorination, cyclization, and palladium-catalyzed coupling. However, the high cost of the raw materials leads to high product costs, which limits the industry's development. The reaction formula is as follows:

[0004]

[0005] According to literature CN114736099, the synthesis of 1-(tert-butyl)-3-chloronaphthalene mainly uses 1-naphthylamine, N-chlorosuccinimide, N-bromosuccinimide, Lewis acid, tert-butyl nitrite, hypophosphite, and lithium tert-butoxide as raw materials, and proceeds through chlorination, bromination, diazotization deamination, and tert-butylation reactions. However, the process is complex, the yield is low, and an expensive palladium catalyst is required to prepare 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane. The reaction formula is as follows:

[0006]

[0007] According to literature CN115974903, the synthesis of 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane mainly uses 2-naphthol, pyridine-2-sulfonyl chloride, tert-butane chloride, and dipinacol boronic acid ester as raw materials, and proceeds through a three-step reaction involving esterification, tert-butylation, and palladium-catalyzed coupling. However, this process requires an expensive palladium catalyst, resulting in high product costs. The reaction formula is as follows:

[0008]

[0009] Existing technologies all require expensive palladium catalysts to prepare 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane, resulting in high product costs and limiting the development of the industry. Summary of the Invention

[0010] (a) Technical problems to be solved

[0011] To address the shortcomings of existing technologies, this invention provides a method for preparing 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane, which has the advantages of inexpensive raw materials, no use of expensive palladium catalysts, and significantly reduced costs.

[0012] (II) Technical Solution

[0013] To achieve the above objectives, the present invention provides the following technical solution: a method for preparing 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane, wherein the reaction formula is as follows:

[0014]

[0015] Includes the following steps:

[0016] S1. Add zinc powder to tetrahydrofuran. Under nitrogen protection, slowly add a tetrahydrofuran solution of TMSCl. After the addition is complete, heat to 60-70℃ and stir for 30 minutes. Add a tetrahydrofuran solution of the compound shown in formula (I) and stir for 1 hour. Add a tetrahydrofuran solution of the compound shown in formula (II) and keep warm and stir overnight. Monitor the reaction for completeness by TLC. Cool to room temperature, filter, wash the filter cake with tetrahydrofuran, cool the filtrate to 0-20℃, add dilute hydrochloric acid to pH=1-5, keep warm and stir for 1 hour, return to room temperature and stir for 1 hour, concentrate under reduced pressure, extract with dichloromethane, wash with saturated brine, dry with anhydrous sodium sulfate, evaporate to dryness, and perform column chromatography to obtain the compound shown in formula (III).

[0017] S2. The compound shown in formula (III) was added to methanol, cooled to 0-10℃, and DBU was added dropwise. After the addition was complete, the mixture was heated to room temperature and stirred overnight. The reaction was monitored by TLC until it was complete. Dilute hydrochloric acid was added dropwise to pH 1-5, the mixture was concentrated under reduced pressure, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain the compound shown in formula (IV).

[0018] S3. The compound shown in formula (IV) was added to acetonitrile, cooled to 0-5℃, phosphorus tribromooxy was added dropwise, the temperature was raised to reflux and stirred overnight, the reaction was monitored by TLC until complete, the reaction solution was added to ice water, distilled under reduced pressure, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and column chromatography was performed to obtain the compound shown in formula (V).

[0019] S4. The compound shown in formula (V) was added to ethylene glycol dimethyl ether and heated to reflux. Solutions of the compound shown in formula (VI) and isoamyl nitrite in ethylene glycol dimethyl ether were prepared separately. The two solutions were added dropwise to the reaction solution simultaneously. After the addition was complete, the mixture was kept warm and stirred overnight. The reaction was monitored by TLC until it was complete. The mixture was cooled to room temperature and quenched with sodium hydroxide aqueous solution. The mixture was extracted with ethyl acetate, washed with saturated sodium bisulfite, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain the compound shown in formula (VII).

[0020] S5. The compound shown in formula (VII) was added to anhydrous tetrahydrofuran, cooled to 0-5℃, and isopropyl magnesium chloride was added dropwise. After the addition was complete, the temperature was raised to room temperature and stirred for 1 h. The temperature was then lowered to -20-30℃, and the compound shown in formula (VIII) was added dropwise. After the addition was complete, the temperature was raised to room temperature and stirred for 1 h. The reaction was monitored by TLC until it was complete. The reaction solution was added to a saturated ammonium chloride aqueous solution, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain the compound shown in formula (XI).

[0021] Preferably, in step S1, the molar ratio of the zinc powder to the compound shown in formula (I) is (2-5):1.

[0022] Preferably, in step S1, the molar ratio of TMSCl to the compound shown in formula (I) is (0.1-0.5):1.

[0023] Preferably, in step S1, the molar ratio of the compound shown in formula (II) to the compound shown in formula (I) is (1.5-4):1.

[0024] Preferably, in step S2, the molar ratio of the DBU to the compound shown in formula (III) is (1.5-4):1.

[0025] Preferably, in step S3, the molar ratio of phosphorus tribromooxy to the compound shown in formula (IV) is (0.5-3):1.

[0026] Preferably, in step S4, the molar ratio of the isoamyl nitrite to the compound shown in formula (V) is (1.5-10):1.

[0027] Preferably, in step S4, the molar ratio of the compound shown in formula (VI) to the compound shown in formula (V) is (1.5-10):1.

[0028] Preferably, in step S5, the molar ratio of the isopropyl magnesium chloride to the compound shown in formula (VII) is (1.2-3):1.

[0029] Preferably, in step S5, the molar ratio of the compound shown in formula (VIII) to the compound shown in formula (VII) is (1.5-4):1.

[0030] (III) Beneficial Effects

[0031] Compared with the prior art, the present invention provides a method for preparing 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane, which has the following beneficial effects:

[0032] 1. The compounds shown in formula (I), formula (II), formula (VI), formula (VIII) and other reagents used in this invention are inexpensive and readily available.

[0033] 2. The method for preparing 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane does not use an expensive palladium catalyst, which can significantly reduce costs. Attached Figure Description

[0034] Figure 1 The 1H NMR spectrum of 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane;

[0035] Figure 2 For the compound shown in formula (IV) 1 HNMR spectrum;

[0036] Figure 3 For the compound shown in formula (V) 1 HNMR spectrum;

[0037] Figure 4 For the compound shown in formula (VII) 1 HNMR spectrum;

[0038] Figure 5 It is 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane 1 HNMR spectrum. Detailed Implementation

[0039] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0040] Example 1:

[0041] A method for preparing 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane

[0042] Synthesis of the compound shown in formula (III):

[0043] 313.4 g of zinc powder was added to 600 mL of tetrahydrofuran. Under nitrogen protection, 34.72 g of TMSCl in 100 mL of tetrahydrofuran solution was slowly added dropwise. After the addition was complete, the temperature was raised to 60-70 °C and stirred for 30 minutes. Then, 200 g of the compound shown in formula (I) in 200 mL of tetrahydrofuran solution was added dropwise. After the addition was complete, the mixture was stirred for 1 hour. Then, 533.68 g of the compound shown in formula (II) in 200 mL of tetrahydrofuran solution was added dropwise. After the addition was complete, the mixture was kept warm and stirred overnight. The reaction was monitored by TLC until it was complete. The mixture was cooled to room temperature, filtered, and the filter cake was washed with tetrahydrofuran. The filtrate was cooled to 0-20 °C, and the pH was adjusted to 1-5 by adding dilute hydrochloric acid. The mixture was kept warm and stirred for 1 hour, then returned to room temperature and stirred for 1 hour. The mixture was concentrated under reduced pressure, extracted with dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 310 g of the compound shown in formula (III), with a yield of 90.5%.

[0044] Synthesis of the compound shown in formula (IV):

[0045] 310 g of the compound shown in formula (III) was added to 1.5 L of methanol, cooled to 0-10 °C, and 440.5 g of DBU was added dropwise. After the addition was complete, the mixture was brought to room temperature and stirred overnight. The reaction was monitored by TLC until complete. The pH was adjusted to 1-5 by adding dilute hydrochloric acid, concentrated under reduced pressure, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 230 g of the compound shown in formula (IV), with a yield of 94.5%.

[0046] Synthesis of the compound shown in formula (V):

[0047] 230 g of the compound shown in formula (IV) was added to 1.2 L of acetonitrile, cooled to 0-5 °C, and 392 g of phosphorus tribromooxygenate was added in portions. The mixture was heated to reflux and stirred overnight. The reaction was monitored by TLC until complete. The reaction solution was added to ice water, distilled under reduced pressure, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to give 300 g of the compound shown in formula (V), with a yield of 94.9%.

[0048] Synthesis of the compound shown in formula (VII):

[0049] 300 g of the compound shown in formula (V) was added to 900 mL of ethylene glycol dimethyl ether, and the mixture was heated to reflux. Solutions of 356 g of the compound shown in formula (VI) in 600 mL of ethylene glycol dimethyl ether and 304 g of isoamyl nitrite in 600 mL of ethylene glycol dimethyl ether were prepared separately. Both solutions were simultaneously added dropwise to the reaction mixture at a uniform rate. After the addition was complete, the mixture was kept warm and stirred overnight. The reaction was monitored by TLC until complete. The mixture was cooled to room temperature, quenched with an aqueous sodium hydroxide solution, extracted with ethyl acetate, washed with saturated sodium bisulfite, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 320 g of the compound shown in formula (VII), with a yield of 93.6%.

[0050] Synthesis of 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane:

[0051] 320 g of the compound shown in formula (VII) was added to 1 L of anhydrous tetrahydrofuran, cooled to 0-5 °C, and 0.91 L of 2 M isopropyl magnesium chloride was added dropwise. After the addition was complete, the mixture was heated to room temperature and stirred for 1 h. The mixture was then cooled to -20 to -30 °C, and 452.5 g of the compound shown in formula (VIII) was added dropwise. After the addition was complete, the mixture was heated to room temperature and stirred for 1 h. The reaction was monitored by TLC until complete. The reaction solution was added to a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 350 g of the compound shown in formula (XI), with a yield of 92.7%.

[0052] Example 2:

[0053] A method for preparing 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane

[0054] Synthesis of the compound shown in formula (III):

[0055] 313.4 g of zinc powder was added to 600 mL of tetrahydrofuran. Under nitrogen protection, 17.36 g of TMSCl in 100 mL of tetrahydrofuran solution was slowly added dropwise. After the addition was complete, the temperature was raised to 60-70 °C and stirred for 30 minutes. Then, 200 g of the compound shown in formula (I) in 200 mL of tetrahydrofuran solution was added dropwise. After the addition was complete, the mixture was stirred for 1 hour. Then, 667 g of the compound shown in formula (II) in 200 mL of tetrahydrofuran solution was added dropwise. After the addition was complete, the mixture was kept warm and stirred overnight. The reaction was monitored by TLC until it was complete. The mixture was cooled to room temperature, filtered, and the filter cake was washed with tetrahydrofuran. The filtrate was cooled to 0-20 °C, and the pH was adjusted to 1-5 by adding dilute hydrochloric acid. The mixture was kept warm and stirred for 1 hour, then returned to room temperature and stirred for 1 hour. The mixture was concentrated under reduced pressure, extracted with dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 315 g of the compound shown in formula (III), with a yield of 92%.

[0056] Synthesis of the compound shown in formula (IV):

[0057] 315 g of the compound shown in formula (III) was added to 1.5 L of methanol, cooled to 0-10 °C, and 330.4 g of DBU was added dropwise. After the addition was complete, the mixture was brought to room temperature and stirred overnight. The reaction was monitored by TLC until complete. The pH was adjusted to 1-5 by adding dilute hydrochloric acid, concentrated under reduced pressure, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 220 g of the compound shown in formula (IV), with a yield of 90.4%.

[0058] Synthesis of the compound shown in formula (V):

[0059] 220 g of the compound shown in formula (IV) was added to 1.2 L of acetonitrile, cooled to 0-5 °C, and 562.5 g of phosphorus tribromooxygenate was added in portions. The mixture was heated to reflux and stirred overnight. The reaction was monitored by TLC until complete. The reaction solution was added to ice water, distilled under reduced pressure, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to give 270 g of the compound shown in formula (V), with a yield of 89.3%.

[0060] Synthesis of the compound shown in formula (VII):

[0061] 270 g of the compound shown in formula (V) was added to 900 mL of ethylene glycol dimethyl ether, and the mixture was heated to reflux. Solutions of 400.5 g of the compound shown in formula (VI) in 600 mL of ethylene glycol dimethyl ether and 342.2 g of isoamyl nitrite in 600 mL of ethylene glycol dimethyl ether were prepared separately. Both solutions were simultaneously added dropwise to the reaction mixture at a uniform rate. After the addition was complete, the mixture was kept warm and stirred overnight. The reaction was monitored by TLC until complete. The mixture was cooled to room temperature, quenched with an aqueous sodium hydroxide solution, extracted with ethyl acetate, washed with saturated sodium bisulfite, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 295 g of the compound shown in formula (VII), with a yield of 95.9%.

[0062] Synthesis of 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane:

[0063] 295 g of the compound shown in formula (VII) was added to 1 L of anhydrous tetrahydrofuran, cooled to 0-5 °C, and 0.68 L of 2 M isopropyl magnesium chloride was added dropwise. After the addition was complete, the mixture was heated to room temperature and stirred for 1 h, then cooled to -20 to -30 °C, and 354.5 g of the compound shown in formula (VIII) was added dropwise. After the addition was complete, the mixture was heated to room temperature and stirred for 1 h. The reaction was monitored by TLC until complete. The reaction solution was added to a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 330 g of the compound shown in formula (XI), with a yield of 94.8%.

[0064] Example 3:

[0065] A method for preparing 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane

[0066] Synthesis of the compound shown in formula (III):

[0067] 522.3 g of zinc powder was added to 600 mL of tetrahydrofuran. Under nitrogen protection, 52 g of TMSCl in 100 mL of tetrahydrofuran solution was slowly added dropwise. After the addition was complete, the temperature was raised to 60-70 °C and stirred for 30 minutes. 200 g of the compound shown in formula (I) in 200 mL of tetrahydrofuran solution was added dropwise. After the addition was complete, the mixture was stirred for 1 hour. 800.5 g of the compound shown in formula (II) in 200 mL of tetrahydrofuran solution was added dropwise. After the addition was complete, the mixture was kept warm and stirred overnight. The reaction was monitored by TLC until complete. The mixture was cooled to room temperature, filtered, and the filter cake was washed with tetrahydrofuran. The filtrate was cooled to 0-20 °C, and the pH was adjusted to 1-5 by adding dilute hydrochloric acid. The mixture was kept warm and stirred for 1 hour, then returned to room temperature and stirred for 1 hour. The mixture was concentrated under reduced pressure, extracted with dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 335 g of the compound shown in formula (III), with a yield of 97.8%.

[0068] Synthesis of the compound shown in formula (IV):

[0069] 335 g of the compound shown in formula (III) was added to 1.5 L of methanol, cooled to 0-10 °C, and 714 g of DBU was added dropwise. After the addition was complete, the mixture was brought to room temperature and stirred overnight. The reaction was monitored by TLC until complete. The pH was adjusted to 1-5 by adding dilute hydrochloric acid, concentrated under reduced pressure, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 250 g of the compound shown in formula (IV), with a yield of 95%.

[0070] Synthesis of the compound shown in formula (V):

[0071] 250 g of the compound shown in formula (IV) was added to 1.2 L of acetonitrile, cooled to 0-5 °C, and 213 g of phosphorus tribromooxygenate was added in portions. The mixture was heated to reflux and stirred overnight. The reaction was monitored by TLC until complete. The reaction solution was added to ice water, distilled under reduced pressure, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to give 300 g of the compound shown in formula (V), with a yield of 87.3%.

[0072] Synthesis of the compound shown in formula (VII):

[0073] 300 g of the compound shown in formula (V) was added to 900 mL of ethylene glycol dimethyl ether, and the mixture was heated to reflux. Solutions of 534.1 g of the compound shown in formula (VI) in 600 mL of ethylene glycol dimethyl ether and 456.2 g of isoamyl nitrite in 600 mL of ethylene glycol dimethyl ether were prepared separately. Both solutions were simultaneously added dropwise to the reaction mixture at a uniform rate. After the addition was complete, the mixture was kept warm and stirred overnight. The reaction was monitored by TLC until complete. The mixture was cooled to room temperature, quenched with an aqueous sodium hydroxide solution, extracted with ethyl acetate, washed with saturated sodium bisulfite, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 320 g of the compound shown in formula (VII), with a yield of 93.6%.

[0074] Synthesis of 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane:

[0075] 320 g of the compound shown in formula (VII) was added to 1 L of anhydrous tetrahydrofuran, cooled to 0-5 °C, and 1.2 L of 2M isopropyl magnesium chloride was added dropwise. After the addition was complete, the mixture was heated to room temperature and stirred for 1 h, then cooled to -20 to -30 °C, and 565.5 g of the compound shown in formula (VIII) was added dropwise. After the addition was complete, the mixture was heated to room temperature and stirred for 1 h. The reaction was monitored by TLC until complete. The reaction solution was added to a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain 355 g of the compound shown in formula (XI), with a yield of 94.1%.

[0076] Although embodiments of the invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made to these embodiments without departing from the principles and spirit of the invention, the scope of which is defined by the appended claims and their equivalents.

Claims

1. A method for preparing 2-(4-(tert-butyl)naphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane, characterized in that, The reaction formula is as follows: ， It includes the following steps: S1. Add zinc powder to tetrahydrofuran. Under nitrogen protection, slowly add a tetrahydrofuran solution of TMSCl. After the addition is complete, heat to 60-70℃ and stir for 30 minutes. Add a tetrahydrofuran solution of the compound shown in formula (I) and stir for 1 hour. Add a tetrahydrofuran solution of the compound shown in formula (II) and keep warm and stir overnight. Monitor the reaction by TLC until complete. Cool to room temperature, filter, wash the filter cake with tetrahydrofuran, cool the filtrate to 0-20℃, add dilute hydrochloric acid to pH=1-5, keep warm and stir for 1 hour, return to room temperature and stir for 1 hour, concentrate under reduced pressure, extract with dichloromethane, wash with saturated brine, dry with anhydrous sodium sulfate, evaporate to dryness, and perform column chromatography to obtain the compound shown in formula (III). S2. The compound shown in formula (III) was added to methanol, cooled to 0-10℃, and DBU was added dropwise. After the addition was complete, the mixture was heated to room temperature and stirred overnight. The reaction was monitored by TLC until it was complete. Dilute hydrochloric acid was added dropwise to pH=1-5, the mixture was concentrated under reduced pressure, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain the compound shown in formula (IV). S3. The compound shown in formula (IV) was added to acetonitrile, cooled to 0-5℃, phosphorus tribromooxygenate was added dropwise, the temperature was raised to reflux and stirred overnight, the reaction was monitored by TLC to ensure complete reaction, the reaction solution was added to ice water, distilled under reduced pressure, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and column chromatography was performed to obtain the compound shown in formula (V). S4. The compound shown in formula (V) was added to ethylene glycol dimethyl ether and heated to reflux. Solutions of the compound shown in formula (VI) and isoamyl nitrite in ethylene glycol dimethyl ether were prepared separately. The two solutions were added dropwise to the reaction solution simultaneously. After the addition was complete, the mixture was kept warm and stirred overnight. The reaction was monitored by TLC until it was complete. The mixture was cooled to room temperature and quenched with sodium hydroxide aqueous solution. The mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium bisulfite, washed with saturated brine, dried with anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain the compound shown in formula (VII). S5. The compound shown in formula (VII) was added to anhydrous tetrahydrofuran, cooled to 0-5℃, and isopropyl magnesium chloride was added dropwise. After the addition was complete, the temperature was raised to room temperature and stirred for 1 h. The temperature was then lowered to -20-30℃, and the compound shown in formula (VIII) was added dropwise. After the addition was complete, the temperature was raised to room temperature and stirred for 1 h. The reaction was monitored by TLC until it was complete. The reaction solution was added to a saturated ammonium chloride aqueous solution, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography to obtain the compound shown in formula (IX).

2. The method for preparing 2-(4-(tert-butyl)naphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane according to claim 1, characterized in that, In step S1, the molar ratio of the zinc powder to the compound shown in formula (I) is (2-5):

1.

3. The method for preparing 2-(4-(tert-butyl)naphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane according to claim 1, characterized in that, In step S1, the molar ratio of TMSCl to the compound shown in formula (I) is (0.1-0.5):

1.

4. The method for preparing 2-(4-(tert-butyl)naphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane according to claim 1, characterized in that, In step S1, the molar ratio of the compound shown in formula (II) to the compound shown in formula (I) is (1.5-4):

1.

5. The method for preparing 2-(4-(tert-butyl)naphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane according to claim 1, characterized in that, In step S2, the molar ratio of the DBU to the compound shown in formula (III) is (1.5-4):

1.

6. The method for preparing 2-(4-(tert-butyl)naphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane according to claim 1, characterized in that, In step S3, the molar ratio of phosphorus tribromooxy to the compound shown in formula (IV) is (0.5-3):

1.

7. The method for preparing 2-(4-(tert-butyl)naphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane according to claim 1, characterized in that, In step S4, the molar ratio of the isoamyl nitrite to the compound shown in formula (V) is (1.5-10):

1.

8. The method for preparing 2-(4-(tert-butyl)naphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane according to claim 1, characterized in that, In step S4, the molar ratio of the compound shown in formula (VI) to the compound shown in formula (V) is (1.5-10):

1.

9. The method for preparing 2-(4-(tert-butyl)naphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane according to claim 1, characterized in that, In step S5, the molar ratio of the isopropyl magnesium chloride to the compound shown in formula (VII) is (1.2-3):

1.

10. The method for preparing 2-(4-(tert-butyl)naphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane according to claim 1, characterized in that, In step S5, the molar ratio of the compound shown in formula (VIII) to the compound shown in formula (VII) is (1.5-4):1.

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