Phenolic hydroxyl compound and preparation method thereof

Abstract

The invention discloses a phenolic hydroxyl compound and a preparation method thereof. The preparation method of the phenolic hydroxyl compound comprises the following step: reacting a halogenated aromatic compound with an alkaline compound in a reaction solvent in an inert gas atmosphere to obtain the phenolic hydroxyl compound. According to the method, the halogen in the halogenated aromatic compound is subjected to electrophilic substitution under the alkaline condition to generate the phenolic hydroxyl compound, the reaction has certain universality, the substituent group of the substrate can be an electron withdrawing group or an electron donating group, an expensive catalyst is not needed, the cost is low, environmental pollution is avoided, and the method is suitable for industrial production. And the method has important significance on drug development and synthesis design.

Description

Technical Field

[0001] The present invention relates to the technical field of organic synthesis, and in particular to a phenolic hydroxyl compound and a preparation method thereof. Background Art

[0002] Aromatic hydroxylation is a powerful synthetic method that is often used to prepare high-value pharmaceuticals, agrochemicals, polymers, and natural products. 2 There are many methods for synthesizing the OH-carbon bond, but considering the cost, operation difficulty and toxicity, the nucleophilic substitution of aromatic hydrocarbons (S N Ar) 3 Reactions are one of the most attractive and commonly used methods.

[0003] In 2002, Daniel M. Green et al. used NaH and 2-(methylsulfonyl)ethanol as reaction conditions to convert fluorides into phenolic compounds, but this method was limited to substrates with electron-withdrawing substituents.

[0004]

[0005] In 2016, Shanghua Xia et al. used copper to catalyze various halogenated hydrocarbons to obtain phenolic compounds. This method no longer limits the substrates to electron-withdrawing substituents but can also be electron-donating substituents. However, the high cost and environmental pollution brought by metal catalysts have become a new problem.

[0006]

[0007] In 2021, Andrew J. Greener and others developed an oxime-based hydroxylation reagent with mild reaction conditions and can react at 30°C, but this reagent is expensive to purchase.

[0008]

[0009] Therefore, developing more universal aromatic hydroxylation reactions that do not require the use of expensive catalysts is an important research direction at present, which is of great significance to both drug development and synthetic design. Summary of the invention

[0010] In view of the deficiencies in the prior art, the purpose of the present invention is to provide a phenolic hydroxyl compound and a preparation method thereof, so as to solve the problems that the current aromatic hydrocarbon hydroxylation reaction is not universal, the catalyst cost is high, and it is easy to cause environmental pollution.

[0011] To achieve the above object, the present invention is implemented through the following technical solutions: In one aspect, the present invention provides a method for preparing a phenolic hydroxyl compound, comprising the following steps: reacting a halogenated aromatic compound and a basic compound in a reaction solvent under an inert gas atmosphere to obtain a phenolic hydroxyl compound; The structural formula of halogenated aromatic compounds is: R-Ar-X; wherein Ar is an aromatic ring, X is a halogen, and R is H, an aromatic ring, and one or more R 4 Any one of a substituted aromatic ring, a carbonyl compound, and a dicarbonyl compound; wherein R 4 Selected from: -NH 2 、-NO 2 , -CHO, -COOH, acetyl, formaldehyde, halogen, alkyl, hydroxy-substituted alkyl, alkoxy, and aryl.

[0012] Preferably, the halogenated aromatic compound is any one of the structures shown below: , , ; Wherein, Ar is an aromatic ring and X is a halogen; Y is O, S, Se, CH 2 、NH、SiH 2 Any of the following: Z is , Any of the following: R 1 , R 2 , R 3 Selected from: H, -NH 2 、-NO 2 , -CHO, -COOH, acetyl, formaldehyde, halogen, alkyl, hydroxy-substituted alkyl, alkoxy, and aryl.

[0013] Preferably, Ar is a pure carbon aromatic ring or an aromatic ring containing heteroatoms.

[0014] Preferably, the pure carbon aromatic ring is selected from any one of phenyl, naphthyl, and anthracenyl; the aromatic ring containing heteroatoms is selected from any one of thienyl, selenophene, tellurol, pyrrolyl, furanyl, thiole, pyridyl, pyranyl, benzofuranyl, benzothiophenyl, indolyl, and quinolyl.

[0015] Preferably, Ar is replaced by one or more R 5 Substituted aromatic ring, R 5 Selected from: -NH 2 、-NO 2 , -CHO, -COOH, acetyl, formaldehyde, halogen, alkyl, hydroxy-substituted alkyl, alkoxy, and aryl.

[0016] Preferably, the basic compound is one or more of potassium tert-butoxide and sodium tert-butoxide.

[0017] Preferably, the reaction solvent is one or more of N,N-dimethylformamide and dimethyl sulfoxide.

[0018] Preferably, the reaction conditions include: reaction temperature of 25-90°C, and reaction time of 5-15 h.

[0019] Preferably, the molar ratio of the halogenated aromatic compound to the basic compound is 1:(2-5).

[0020] Preferably, X is any one of fluorine, chlorine and bromine, more preferably fluorine.

[0021] Preferably, the above steps further include separating and purifying the mixture obtained after the reaction; the separation and purification includes: extracting and column chromatography the mixture in sequence to obtain phenolic hydroxyl compounds; or adjusting the pH of the mixture to acidic, and then extracting and column chromatography in sequence to obtain phenolic hydroxyl compounds.

[0022] In a second aspect, the present invention further provides a phenolic hydroxy compound, which is prepared by the preparation method of the phenolic hydroxy compound described in the first aspect.

[0023] The beneficial effects of the present invention are: The present invention provides a method for preparing phenolic hydroxyl compounds. A carbon-halogen bond substitution reaction can be achieved by reacting a halogenated aromatic compound and an alkaline compound in a solvent to generate a phenolic hydroxyl substituent, thereby converting the halogenated aromatic compound into a phenolic hydroxyl compound. The reaction has certain universality. The substituent of the halogenated aromatic compound can be an electron-withdrawing group or an electron-donating group. There is no need to use an expensive catalyst, the cost is low, and no environmental pollution is caused. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] In order to more clearly illustrate the technical solution of the embodiment of the present invention, the drawings of the embodiment are briefly introduced below.

[0025] Figure 1 This is the H NMR spectrum of TPT-FOH of Example 1; Figure 2 This is the NMR carbon spectrum of TPT-FOH in Example 1; Figure 3 is the H NMR spectrum of NA-OH in Example 2; Figure 4 is the NMR carbon spectrum of NA-OH in Example 2; Figure 5 This is the H NMR spectrum of TPT-2OH in Example 3; Figure 6 This is the NMR carbon spectrum of TPT-2OH in Example 3; Figure 7 This is the H NMR spectrum of Benz-2OH in Example 4; Figure 8 This is the NMR carbon spectrum of Benz-2OH in Example 4; Fig. 9 This is the H NMR spectrum of Ph-2OH in Example 5; Fig.10 This is the NMR carbon spectrum of Ph-2OH in Example 5; Fig.11 This is the H NMR spectrum of Ph-NH2OH in Example 6; Fig.12 This is the NMR carbon spectrum of Ph-NH2OH in Example 6; Fig.13 This is the H NMR spectrum of Ph-OHCHO in Example 7; Fig.14 This is the NMR carbon spectrum of Ph-OHCHO in Example 7; Fig.15 is the H NMR spectrum of Benz-OH in Example 8; Fig.16 This is the carbon NMR spectrum of Benz-OH in Example 8. DETAILED DESCRIPTION

[0026] The following will be combined with the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0027] In the process of carbon-halogen bond substitution reaction to generate phenolic hydroxyl substituents, carbon-halogen bonds, especially CF bonds, have large bond energy (485.3 kJ / mol), short bond length (1.38 Å), and small van der Waals radius ( r w = 1.47 Å), making their activation and conversion very difficult. Therefore, the sustainable degradation of these fluorinated artificial molecules with the strongest dissociation energy chemical bonds (~ 126 kcal / mol) becomes a huge challenge, resulting in their accumulation in the environment and delayed renewability. In order to promote the cyclic chemistry of fluorine, great efforts have been made to achieve the activation and conversion of C-F bonds. At present, expensive precious metal catalysts are mostly used when C-F bonds are broken to generate phenolic compounds, resulting in high costs, complex reaction processes, and easy environmental pollution.

[0028] In view of this, an embodiment of the present invention provides a method for preparing a phenolic hydroxyl compound, comprising the following steps: reacting a halogenated aromatic compound and a basic compound in a reaction solvent under an inert gas atmosphere to obtain a phenolic hydroxyl compound; the halogenated aromatic compound has a structural formula of: R-Ar-X; wherein Ar is an aromatic ring, X is a halogen, and R is H, an aromatic ring, and one or more R 4 Any one of a substituted aromatic ring, a carbonyl compound, and a dicarbonyl compound; wherein R 4 Selected from: -NH 2 、-NO 2 , -CHO, -COOH, acetyl, formaldehyde, halogen, alkyl, hydroxy-substituted alkyl, alkoxy, and aryl.

[0029] In some embodiments, the halogenated aromatic compound is any one of the following structures: , , ; Wherein, Ar is an aromatic ring and X is a halogen; Y is O, S, Se, CH 2 、NH、SiH 2 Any of the following: Z is , Any of the following: R 1 , R 2 , R 3 Selected from: H, -NH 2 、-NO 2 , -CHO, -COOH, acetyl, formaldehyde, halogen, alkyl, hydroxy-substituted alkyl, alkoxy, and aryl.

[0030] In some embodiments, Ar is a pure carbon aromatic ring or an aromatic ring containing heteroatoms. The pure carbon aromatic ring is selected from any one of phenyl, naphthyl, and anthracenyl; the aromatic ring containing heteroatoms is selected from any one of thienyl, selenophene, tellurol, pyrrolyl, furanyl, thiolyl, pyridyl, pyranyl, benzofuranyl, benzothiophenyl, indolyl, and quinolyl.

[0031] In some embodiments, Ar is replaced by one or more R 5 Substituted aromatic ring, R 5 Selected from: -NH 2 、-NO 2 , -CHO, -COOH, acetyl, formaldehyde, halogen, alkyl, hydroxy-substituted alkyl, alkoxy, and aryl.

[0032] In some embodiments, the alkaline compound is one or more of potassium tert-butoxide and sodium tert-butoxide; the reaction solvent is one or more of N,N-dimethylformamide and dimethyl sulfoxide; the reaction temperature is 25-90°C, and the reaction time is 5-15 h. Specifically, the reaction temperature can be room temperature or heated to increase the yield, and the reaction temperature is 25°C, 30°C, 35°C, 40°C, 45°C, 50°C, 55°C, 60°C, 70°C, 75°C, 80°C, 90°C or any temperature within the above range. In the preparation method of the present invention, the reaction time is not particularly limited, and the appropriate reaction time can be determined by detecting whether the raw material remains by TLC method, which is usually 5-15h, such as 5h, 5.5h, 6h, 6.5h, 7h, 8h, 10h, 12h, 15h or any time within the above range.

[0033] In some embodiments, the molar ratio of the halogenated aromatic compound to the basic compound is 1:(2-5). The molar ratio of the halogenated aromatic compound to the basic compound is selected according to the number of hydroxyl groups to be substituted, and can be 1:2, 1:2.5, 1:3, 1:3.5, 1:4, 1:4.5, 1:5 or any ratio within the above range.

[0034] In some embodiments, a method for preparing a phenolic hydroxyl compound, the synthesis route is shown in Formula 1, and specifically comprises the following steps: under an inert gas atmosphere, compound I and a basic compound (potassium tert-butoxide and / or sodium tert-butoxide) are heated to 25-75° C. in DMF or DMSO for reaction for 5-8 h, then extracted, and separated by column chromatography to obtain the target product; wherein the molar ratio of compound I to the basic compound is 1:(2-5).

[0035] (1) In some embodiments, a method for preparing a phenolic hydroxyl compound, the synthesis route is shown in Formula 2, and specifically comprises the following steps: under an inert gas atmosphere, compound II and a basic compound (potassium tert-butoxide and / or sodium tert-butoxide) are heated to 50-75° C. in DMF or DMSO for reaction for 5-8 h, then extracted, dried, and separated by column chromatography to obtain the target product; wherein the molar ratio of compound II to the base is 1:(2-2.5).

[0036] (2) In some embodiments, a method for preparing a phenolic hydroxyl compound, the synthetic route is shown in formula (3), and specifically comprises the following steps: under an inert gas atmosphere, compound III and a basic compound (potassium tert-butoxide and / or sodium tert-butoxide) are reacted in DMF or DMSO at 25-90° C. for 5-15 h, then extracted, dried, and separated by column chromatography to obtain the target product; wherein the molar ratio of compound III to the base is 1:(2-5).

[0037] (3) In some embodiments, the solvent used for extraction is water and ethyl acetate, or water and dichloromethane.

[0038] In some preferred embodiments, after the heating reaction is completed, a protonic acid is added to the reaction system to adjust the pH to acidic, the reaction is continued for 1-5 hours, and then an extraction operation is performed.

[0039] In some embodiments, after extraction and column chromatography, the product may be further subjected to recrystallization.

[0040] The preparation method of the phenolic hydroxyl compound of the present invention is further described in detail below in conjunction with specific examples.

[0041] Example 1 Synthesis of TPT-FOH

[0042] The synthesis method comprises the following steps: TPT-DF (424 mg, 1 mmol) and potassium tert-butoxide (224 mg, 2 mmol) were added to a 50 mL two-necked flask, and then argon was introduced. 30 mL N,N-dimethylformamide was added under argon atmosphere. The mixture was reacted at 75 °C for 5 hours, cooled to room temperature, and a large amount of water and ethyl acetate were added. After extraction, drying, and filtration, the white solid product TPT-FOH (220 mg, 52%) was obtained by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 10:1). Figure 1~2 As shown, its characterization data: 1 H NMR (400 MHz, DMSO-d6) δ 9.57 (d, J = 2.4 Hz, 1H), 7.24 (q, J =5.3 Hz, 3H), 7.20 - 7.16 (m, 5H), 7.00 (ddd, J = 9.5, 7.5, 4.7 Hz, 8H), 6.67(dd, J = 8.7, 2.6 Hz, 2H). 13C NMR (100 MHz, DMSO) δ 160.24, 157.64, 139.84,139.13, 137.88, 137.04, 136.52, 134.05, 133.01, 132.93, 130.93, 130.57,129.13, 129.03, 128.50, 127.95, 127.48, 124.38, 115.93, 115.41, 115.20. Example 2 Synthesis of NA-OH

[0043] The synthesis method comprises the following steps: Potassium tert-butoxide (224 mg, 2 mmol) was added to a two-necked flask, and then argon was introduced. 30 mL of N,N-dimethylformamide and 2-fluoronaphthalene (146 mg, 1 mmol) were added with a syringe under argon atmosphere. Stir at 75 °C for 5 hours, cool to room temperature, add a large amount of water and ethyl acetate, extract, dry, filter, and separate by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 5:1) to obtain the target product NA-OH (70 mg, 48.5 %). Figure 3~4 As shown, its characterization data: 1 H NMR (400 MHz, DMSO-d 6 ) δ 10.10 (t, J = 0.9 Hz, 1H), 8.21 - 8.07(m, 1H), 7.84 - 7.75 (m, 1H), 7.52 - 7.40 (m, 2H), 7.37 - 7.26 (m, 2H), 6.88(dt, J = 7.0, 1.4 Hz, 1H). 13 C NMR (100 MHz, DMSO-d 6 ) δ 155.80, 155.74, 134.56,134.49, 134.44, 131.06, 131.00, 127.94, 127.88, 127.82, 127.77, 126.67,126.61, 126.60, 126.49, 126.36, 125.14, 125.09, 125.02, 114.87, 114.83,113.01, 112.96, 112.90. Example 3 Synthesis of TPT-2OH

[0044] The synthesis method comprises the following steps: TPT-TF (460 mg, 1 mmol) and potassium tert-butoxide (337 mg, 3 mmol) were added to a two-necked flask, and then argon was introduced. 30 mL of N,N-dimethylformamide was added under argon atmosphere. Stir at 75 °C for 5 hours, cool to room temperature, add a large amount of water and ethyl acetate, extract, dry, filter, and separate by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 10:1) to obtain the target product TPT-2OH (245 mg, 53.6%). Figures 5 and 6 As shown, the characterization data: 1 H NMR (400 MHz, DMSO-d6) δ 9.61 (s, 2H), 6.99 (dd, J = 7.3, 3.0 Hz, 12H), 6.68 - 6.59 (m, 4H). 13 C NMR (100 MHz, DMSO) δ 161.72, 161.59, 159.17, 156.45,136.86, 136.49, 132.03, 131.99, 131.93, 131.85, 129.44, 123.44, 114.83,114.40, 114.19. Example 4 Synthesis of Benz-2OH

[0045] The synthesis method comprises the following steps: Add bis(4-fluorophenyl)methanone (218 mg, 1 mmol) and potassium tert-butoxide (224 mg, 2 mmol) to a two-necked flask, add 30 mL of N,N-dimethylformamide under argon atmosphere, stir and react at 75 °C for 5 hours, cool to room temperature, add water first, then add 5 wt% HCl solution to adjust the solution to acidity, stir for 2 hours, extract with ethyl acetate and water, dry and filter, and separate by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 5:1) to obtain the target product bis(4-hydroxyphenyl)methanone (101 mg, 47.1%). Figure 7-8 As shown, its characterization data: 1 H NMR (400MHz, DMSO-d 6 ) δ 10.29 (s, 2H), 7.68 - 7.57 (m, 4H), 6.95 - 6.86 (m, 4H).13 CNMR (100 MHz, DMSO-d 6 ) δ 194.79, 162.49, 138.59, 133.01, 132.30, 132.25,129.62, 128.86, 128.82, 128.37, 115.74. Example 5 Synthesis of Benz-2OH

[0046] The synthesis method comprises the following steps: o-Difluorobenzene (114 mg, 1 mmol) and potassium tert-butoxide (224 mg, 2 mmol) were added to a two-necked flask, and 30 mL of N,N-dimethylformamide was added under an argon atmosphere. The mixture was stirred at 90 °C for 15 hours, cooled to room temperature, and water was added first, followed by 5 wt% HCl solution to adjust the solution to acidity. After stirring for 1 hour, the mixture was extracted with ethyl acetate and water. After drying and filtering, the target product, catechol (31 mg, 28.2 %), was obtained by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 4:1). Figures 9 and 10 As shown, its characterization data: 1 H NMR (400 MHz, DMSO- d 6 ) δ8.82 (d, J = 5.7 Hz, 2H), 6.76 (ddd, J = 13.8, 7.4, 3.3 Hz, 2H), 6.62 (tq, J = 7.0,3.5 Hz, 2H). 13 C NMR (100 MHz, DMSO) δ 145.74, 119.92, 119.78, 116.22, 116.17. Example 6 Ph-NH 2 Synthesis of OH

[0047] The synthesis method comprises the following steps: 3-Fluoroaniline (111 mg, 1 mmol) and potassium tert-butoxide (224 mg, 2 mmol) were added to a two-necked flask, and 30 mL of N,N-dimethylformamide was added under an argon atmosphere. The mixture was stirred at room temperature for 6 hours, and water was added. Subsequently, 5 wt% HCl solution was added to adjust the solution to acidity. After stirring for 1 hour, the mixture was extracted with ethyl acetate and water. After drying and filtering, the target product 3-aminophenol (51 mg, 28.2 %) was obtained by separation by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 5:1). Figures 11-12 As shown, its characterization data: 1 H NMR (400 MHz, DMSO- d 6 ) δ 8.88 (s, 1H), 6.80 (t, J = 7.8 Hz, 1H), 6.08 – 6.01 (m, 2H), 5.98 (ddd, J = 8.0, 2.3, 1.1 Hz,1H), 4.83 (s, 2H). 13 C NMR (100 MHz, DMSO) δ 158.53, 150.21, 130.05, 106.08,104.00, 101.56. Example 7 Synthesis of Ph-OHCHO

[0048] The synthesis method comprises the following steps: 4-Fluorobenzaldehyde (124 mg, 1 mmol) and potassium tert-butoxide (224 mg, 2 mmol) were added to a two-necked flask, and 50 mL of N,N-dimethylformamide was added under an argon atmosphere. The mixture was stirred at room temperature for 6 hours, and water was added. Subsequently, 5 wt% HCl solution was added to adjust the solution to acidity. After stirring for 1 hour, the solution was extracted with ethyl acetate, dried, filtered, and separated by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 10:1) to obtain the target product 4-hydroxybenzaldehyde (63 mg, 51.6 %). Figures 13 and 14 As shown, its characterization data: 1 H NMR (400 MHz, DMSO- d 6 ) δ 10.61 (s,1H), 9.80 (d, J = 2.6 Hz, 1H), 7.77 (dd, J= 8.6, 2.4 Hz, 2H), 6.95 (d, J = 8.4 Hz,2H). 13 C NMR (100 MHz, DMSO) δ 191.43, 191.36, 163.80, 132.58, 128.91, 116.32. Example 8 Synthesis of Benz-OH

[0049] The synthesis method comprises the following steps: 4-Fluorobenzophenone (200 mg, 1 mmol) and potassium tert-butoxide (224 mg, 2 mmol) were added to a two-necked flask, and 30 mL of N,N-dimethylformamide was added under an argon atmosphere. The mixture was stirred at 75 °C for 5 hours, cooled to room temperature, and water was added first, followed by 5 wt% HCl solution to adjust the solution to acidity. After stirring for 2 hours, the mixture was extracted with ethyl acetate, dried, filtered, and separated by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 8:1) to obtain the target product 4-hydroxybenzophenone (112 mg, 56.6 %). Figures 15 and 16 As shown, its characterization data: 1 H NMR (400 MHz, DMSO- d 6 )δ 10.45 (d, J = 3.4 Hz, 1H), 7.75 - 7.58 (m, 5H), 7.58 - 7.44 (m, 2H), 6.91(dd, J = 8.9, 2.8 Hz, 2H). 13 C NMR (100 MHz, DMSO) δ 194.80, 162.49, 138.60, 133.00, 132.28, 132.25, 129.61, 128.85, 128.82, 128.39, 115.74. Compared with the current synthesis conditions of phenolic hydroxyl, the advantages of the present invention are as follows: ① The synthesis process is pollution-free, and the reagents used are environmentally friendly reagents after extraction. ② Low cost, potassium tert-butoxide and DMF are both cheap and easily available reagents. ③ Mild reaction conditions, the reaction can be carried out at 50-75°C or even room temperature, while other similar reactions are often carried out at above 120°C. ④ No metal catalyst is used, the reaction conditions are simple, easy to operate, and the yield is high.

[0050] It should be noted that the above embodiments all belong to the same inventive concept, and the description of each embodiment has its own focus. For matters that are not described in detail in some embodiments, reference may be made to the description in other embodiments.

[0051] The above-mentioned embodiments only express the implementation methods of the present invention, and the descriptions thereof are relatively specific and detailed, but they cannot be understood as limiting the scope of the invention patent. It should be pointed out that, for ordinary technicians in this field, several variations and improvements can be made without departing from the concept of the present invention, which all belong to the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention shall be subject to the attached claims.

Claims

1. A method for preparing a phenolic hydroxyl compound, characterized in that: The following steps are involved: Under an inert gas atmosphere, a halogenated aromatic compound and a basic compound are reacted in a reaction solvent to obtain a phenolic hydroxy compound; The structural formula of the halogenated aromatic compound is: R-Ar-X; In the formula, Ar is an aromatic ring, X is a halogen, and R is any one of H, an aromatic ring, an aromatic ring substituted by one or more R4, a carbonyl compound, and a dicarbonyl compound; wherein R4 is selected from any one of -NH2, -NO2, -CHO, -COOH, acetyl, formaldehyde, halogen, alkyl, alkyl substituted by hydroxyl, alkoxy, and aryl.

2. The method for preparing a phenolic hydroxy compound according to claim 1, characterized in that: The halogenated aromatic compound is any one of the following structures: ， ， ； Wherein, Ar is an aromatic ring and X is a halogen; Y is any one of O, S, Se, CH2, NH, and SiH2; Z is , Any of the following: R1, R2, and R3 are selected from any one of: H, -NH2, -NO2, -CHO, -COOH, acetyl, formaldehyde, halogen, alkyl, hydroxy-substituted alkyl, alkoxy, and aryl.

3. The method for preparing a phenolic hydroxy compound according to claim 1, characterized in that: Ar is a pure carbon aromatic ring or an aromatic ring containing heteroatoms.

4. The method for preparing a phenolic hydroxy compound according to claim 3, characterized in that: The pure carbon aromatic ring is selected from any one of phenyl, naphthyl, and anthracene; the aromatic ring containing heteroatoms is selected from any one of thienyl, selenophene, tellurol, pyrrolyl, furanyl, thiole, pyridyl, pyranyl, benzofuranyl, benzothiophenyl, indolyl, and quinolyl.

5. The method for preparing a phenolic hydroxy compound according to claim 2, characterized in that: Ar is an aromatic ring substituted by one or more R5, and R5 is selected from any one of: -NH2, -NO2, -CHO, -COOH, acetyl, formaldehyde, halogen, alkyl, alkyl substituted by hydroxyl, alkoxy, and aryl.

6. The method for preparing a phenolic hydroxy compound according to claim 1, characterized in that: The alkaline compound is one or more of potassium tert-butoxide and sodium tert-butoxide; the molar ratio of the halogenated aromatic compound to the alkaline compound is 1:(2-5).

7. The method for preparing a phenolic hydroxy compound according to claim 1, characterized in that: The reaction solvent is one or more of N,N-dimethylformamide and dimethyl sulfoxide.

8. The method for preparing a phenolic hydroxy compound according to claim 1, wherein The reaction conditions include: reaction temperature of 25-90° C., and reaction time of 5-15 h.

9. The method for preparing a phenolic hydroxy compound according to claim 1, characterized in that: The method also includes separating and purifying the mixture obtained after the reaction is completed; the separation and purification includes the following steps: The mixture is subjected to extraction and column chromatography in sequence to obtain the phenolic hydroxyl compound; or, The pH of the mixture is adjusted to acidic, and then extraction and column chromatography are performed in sequence to obtain the phenolic hydroxyl compound.

10. A phenolic hydroxy compound, characterized in that: The phenolic hydroxy compound is prepared by the preparation method of any one of claims 1 to 9.

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