CN116425782A - Preparation method of 5-acetyl-2-fluorobenzeneboronic acid pinacol ester - Google Patents

Preparation method of 5-acetyl-2-fluorobenzeneboronic acid pinacol ester Download PDF

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CN116425782A
CN116425782A CN202310285965.9A CN202310285965A CN116425782A CN 116425782 A CN116425782 A CN 116425782A CN 202310285965 A CN202310285965 A CN 202310285965A CN 116425782 A CN116425782 A CN 116425782A
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acetyl
fluorobenzeneboronic acid
pinacol ester
bromo
magnesium sulfate
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范江涛
孙林
李晓杰
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Yantai Shengkailun Chemical Technology Co ltd
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    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
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    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Abstract

The invention relates to the technical field of organic synthesis, and discloses a preparation method of 5-acetyl-2-fluorobenzeneboronic acid pinacol ester, which is characterized in that 3-bromo-4-fluorobenzoketone, triethyl orthoformate and ethylene glycol are reacted to synthesize 3-bromo-4-fluoroacetophenone ethylene glycol, then the 3-bromo-4-fluoroacetophenone ethylene glycol is reacted with n-butyllithium and a boration reagent, and subjected to hydrochloric acid hydrolysis to obtain 5-acetyl-2-fluorobenzeneboronic acid, and finally the 5-acetyl-2-fluorobenzeneboronic acid pinacol ester is reacted with pinacol. The preparation method is novel, simple and efficient, has mild reaction conditions and no pollution, has high yield of target products, high yield and good purity, and is suitable for industrial production.

Description

Preparation method of 5-acetyl-2-fluorobenzeneboronic acid pinacol ester
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of 5-acetyl-2-fluorobenzeneboronic acid pinacol ester.
Background
The pinacol ester compound containing the fluorobenzene boric acid is an important intermediate, can be used for synthesizing compounds such as an antibacterial agent, a herbicide, a medicament and the like, and is widely applied to the fields of agriculture, medicine and the like; the synthesis of the pinacol ester compound containing the fluorobenzeneboronic acid by a simple and efficient method has important significance, as in the patent CN113372369A 'preparation method of 2-formyl-4-fluorobenzeneboronic acid pinacol ester', a non-palladium catalytic decarboxylation and boronation reaction is carried out by taking carboxylate as a substrate and isonicotinic acid ester as a catalyst, so as to obtain the 2-formyl-4-fluorobenzeneboronic acid pinacol ester. For example, the literature 2-morpholino-5-difluoromethyl phenylboronic acid pinacol ester is prepared from 3-bromo-4-fluorobenzaldehyde as a raw material by fluorination, substitution and organolithium reaction; the invention aims to synthesize a novel 5-acetyl-2-fluorobenzeneboronic acid pinacol ester compound by taking cheap and easily available 3-bromo-4-fluorobenzone, triethyl orthoformate, a boration reagent, pinacol and the like as reactants.
Disclosure of Invention
(one) solving the technical problems
The invention provides 5-acetyl-2-fluorobenzeneboronic acid pinacol ester with high yield and good purity and a preparation method thereof.
(II) technical scheme
In order to achieve the above purpose, the present invention provides the following technical solutions:
a preparation method of 5-acetyl-2-fluorobenzeneboronic acid pinacol ester:
s1, sequentially adding 3-bromo-4-fluorobenzoketone, triethyl orthoformate and ethylene glycol into a reaction bottle, then adding a catalyst p-toluenesulfonic acid, reacting at constant temperature of 25-35 ℃ in a nitrogen atmosphere for 4-8 h, adding saturated sodium bicarbonate solution after the reaction, standing for layering, extracting and separating an upper water phase, then adding dichloromethane, standing for layering, extracting and separating a lower organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering, taking filtrate, rectifying, controlling the vacuum degree to be 0.1-0.15 MPa, and controlling the temperature to be 152-156 ℃ to obtain the 3-bromo-4-fluoroacetophenone ethylene glycol.
S2, adding 3-bromo-4-fluoro acetophenone glycol and a boration reagent into an organic solvent, dropwise adding a solution of n-butyllithium in a low-temperature reactor under nitrogen atmosphere, reacting 2-4-h, dropwise adding a dilute hydrochloric acid solution after the reaction to adjust the pH to 1-2, standing for 6-18 h, concentrating under reduced pressure to remove the organic solvent, adding ethyl acetate and water, standing for layering, extracting and separating to obtain an ethyl acetate organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, washing a crude product with a mixed solution of dichloromethane and petroleum ether, and recrystallizing with a mixed solution of methanol and water to obtain the 5-acetyl-2-fluorobenzeneboric acid.
S3, dissolving 5-acetyl-2-fluorobenzeneboronic acid and pinacol into tetrahydrofuran, then adding magnesium sulfate, reacting 4-8 h, filtering to remove magnesium sulfate, concentrating under reduced pressure to remove solvent, adding the crude product into toluene and water, and extracting and separating to obtain a toluene organic phase; then adding saturated saline, extracting and separating to obtain a toluene organic phase, adding magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, and washing with n-hexane to obtain the 5-acetyl-2-fluorobenzeneboronic acid pinacol ester.
Preferably, the molar ratio of 3-bromo-4-fluorobenzone, triethyl orthoformate and ethylene glycol in S1 is 1:1.3-1.8:1.7-2.4.
Preferably, the catalyst p-toluenesulfonic acid in S1 is 1-1.3% of the total mass of the reactants.
4. The method for preparing 5-acetyl-2-fluorobenzeneboronic acid pinacol ester according to claim 1, which is characterized in that: the organic solvent in S2 comprises tetrahydrofuran, 1, 4-dioxane or acetone.
Preferably, the reaction mole ratio of the 3-bromo-4-fluoro acetophenone glycol, the boration reagent and the n-butyl lithium in the S2 is 1:1-1.3:1.2-1.8.
Preferably, the boration agent in S2 comprises tributyl borate or triisopropyl borate.
Preferably, the reaction mole ratio of the 5-acetyl-2-fluorobenzeneboronic acid, pinacol and magnesium sulfate in the S3 is 1:1-1.5:2-2.8.
(III) beneficial technical effects
The invention synthesizes 3-bromo-4-fluoro acetophenone ethylene glycol by the reaction of cheap and easily available 3-bromo-4-fluoro benzophenone, triethyl orthoformate and ethylene glycol, then reacts with n-butyl lithium and boration reagent, and is hydrolyzed by hydrochloric acid to obtain 5-acetyl-2-fluoro phenylboronic acid, and finally reacts with pinacol to obtain the target product 5-acetyl-2-fluoro phenylboronic acid pinacol ester. The preparation and purification method is novel, simple and efficient, has mild reaction conditions and no pollution, has high yield of target products, high yield and good purity, and is suitable for industrial production.
Drawings
FIG. 1 is a scheme showing the preparation of pinacol ester of 5-acetyl-2-fluorophenylboronic acid.
Description of the embodiments
Examples
S1, sequentially adding 20 mmol of 3-bromo-4-fluorobenzoketone, 26 mmol of triethyl orthoformate and 40 mmol of ethylene glycol into a reaction bottle, then adding a catalyst p-toluenesulfonic acid which is 1.3% of the total mass of reactants, reacting at constant temperature in a nitrogen atmosphere for 8 h, adding saturated sodium bicarbonate solution after the reaction, standing for layering, extracting and separating an upper water phase, then adding dichloromethane, standing for layering, extracting and separating a lower organic phase, adding anhydrous magnesium sulfate for drying and dehydrating, filtering, taking filtrate, rectifying, controlling the vacuum degree to be 0.15 MPa, and controlling the temperature to be 155 ℃ to obtain the 3-bromo-4-fluoroacetophenone ethylene glycol.
S2, adding 10 mmol of 3-bromo-4-fluoro acetophenone ethylene glycol and 12 mmol of triisopropyl borate into 1, 4-dioxane, dropwise adding a tetrahydrofuran solution containing 15 mmol of n-butyllithium in a low-temperature reactor under nitrogen atmosphere, reacting 4. 4 h, dropwise adding a dilute hydrochloric acid solution to adjust the pH value to 2 after the reaction, standing for 6. 6 h, concentrating under reduced pressure to remove an organic solvent, adding ethyl acetate and water, standing for layering, extracting and separating an ethyl acetate organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering and concentrating the filtrate under reduced pressure, washing the crude product with a mixed solution of dichloromethane and petroleum ether, and recrystallizing with a mixed solution of methanol and water to obtain 5-acetyl-2-fluorobenzeneboronic acid, wherein the yield is 1.76 g and 96.7%.
S3, dissolving 20 mmol of 5-acetyl-2-fluorobenzeneboronic acid and 20 mmol of pinacol into tetrahydrofuran, then adding 56 mmol of magnesium sulfate, reacting 8 h, filtering to remove magnesium sulfate, concentrating under reduced pressure to remove a solvent, adding a crude product into toluene and water, and extracting and separating to obtain a toluene organic phase; then adding saturated saline, extracting and separating to obtain a toluene organic phase, adding magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, and washing with n-hexane to obtain the 5-acetyl-2-fluorobenzeneboronic acid pinacol ester, wherein the yield is 4.77 and g, and the yield is 90.3%.
Examples
S1, sequentially adding 20 mmol of 3-bromo-4-fluorobenzoketone, 32 mmol of triethyl orthoformate and 45mmol of ethylene glycol into a reaction bottle, then adding a catalyst p-toluenesulfonic acid accounting for 1% of the total mass of reactants, reacting at constant temperature in a nitrogen atmosphere for 6 h, adding a saturated sodium bicarbonate solution after the reaction, standing for layering, extracting and separating to obtain an upper water phase, then adding dichloromethane, standing for layering, extracting and separating to obtain a lower organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering and obtaining filtrate, rectifying, controlling the vacuum degree to be 0.15 MPa, and controlling the temperature to be 156 ℃ to obtain the 3-bromo-4-fluoroacetophenone ethylene glycol.
S2, adding 10 mmol of 3-bromo-4-fluoro acetophenone ethylene glycol and 11 mmol of triisopropyl borate into tetrahydrofuran, dropwise adding a tetrahydrofuran solution containing 12 mmol of n-butyllithium in a low-temperature reactor under nitrogen atmosphere, reacting 3 h, dropwise adding a dilute hydrochloric acid solution to adjust the pH value to 2 after the reaction, standing for 12 h, concentrating under reduced pressure to remove an organic solvent, adding ethyl acetate and water, standing for layering, extracting and separating an ethyl acetate organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, washing a crude product with a mixed solution of dichloromethane and petroleum ether, and recrystallizing with a mixed solution of methanol and water to obtain the 5-acetyl-2-fluorobenzeneboric acid.
S3, dissolving 20 mmol of 5-acetyl-2-fluorobenzeneboronic acid and 23 mmol of pinacol into tetrahydrofuran, then adding 50 mmol of magnesium sulfate, reacting 6 h, filtering to remove magnesium sulfate, concentrating under reduced pressure to remove a solvent, adding a crude product into toluene and water, and extracting and separating to obtain a toluene organic phase; then adding saturated saline, extracting and separating to obtain a toluene organic phase, adding magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, and washing with n-hexane to obtain the 5-acetyl-2-fluorobenzeneboronic acid pinacol ester.
Examples
S1, sequentially adding 20 mmol of 3-bromo-4-fluorobenzoketone, 26 mmol of triethyl orthoformate and 34 mmol of ethylene glycol into a reaction bottle, then adding p-toluenesulfonic acid serving as a catalyst accounting for 1% of the total mass of reactants, reacting at constant temperature in a nitrogen atmosphere for 4. 4 h, adding saturated sodium bicarbonate solution after the reaction, standing for layering, extracting and separating to obtain an upper water phase, then adding dichloromethane, standing for layering, extracting and separating to obtain a lower organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering and obtaining filtrate, rectifying, controlling the vacuum degree to be 0.1 MPa, and obtaining the 3-bromo-4-fluoroacetophenone ethylene glycol at the temperature of 152 ℃, wherein the yield is 5.11 g, and the yield is 98.3%.
S2, adding 10 mmol of 3-bromo-4-fluoro acetophenone ethylene glycol and 12 mmol of tributyl borate into acetone, dropwise adding an acetone solution containing 18 mmol of n-butyllithium in a low-temperature reactor under nitrogen atmosphere, reacting 2, h, dropwise adding a dilute hydrochloric acid solution to adjust the pH value to 1 after the reaction, standing 18, h, concentrating under reduced pressure to remove an organic solvent, adding ethyl acetate and water, standing for layering, extracting and separating an ethyl acetate organic phase, adding anhydrous magnesium sulfate for drying, removing water, filtering, concentrating the filtrate under reduced pressure, washing a crude product with a mixed solution of dichloromethane and petroleum ether, and recrystallizing with a mixed solution of methanol and water to obtain the 5-acetyl-2-fluorobenzeneboric acid.
S3, dissolving 20 mmol of 5-acetyl-2-fluorobenzeneboronic acid and 20 mmol of pinacol into tetrahydrofuran, then adding 45mmol of magnesium sulfate, reacting 8 h, filtering to remove magnesium sulfate, concentrating under reduced pressure to remove a solvent, adding a crude product into toluene and water, and extracting and separating to obtain a toluene organic phase; then adding saturated saline, extracting and separating to obtain a toluene organic phase, adding magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, and washing with n-hexane to obtain the 5-acetyl-2-fluorobenzeneboronic acid pinacol ester.
Examples
S1, sequentially adding 20 mmol of 3-bromo-4-fluorobenzoketone, 26 mmol of triethyl orthoformate and 48 mmol of ethylene glycol into a reaction bottle, then adding a catalyst p-toluenesulfonic acid accounting for 1% of the total mass of reactants, reacting at constant temperature in a nitrogen atmosphere for 4 h, adding a saturated sodium bicarbonate solution after the reaction, standing for layering, extracting and separating to obtain an upper water phase, then adding dichloromethane, standing for layering, extracting and separating to obtain a lower organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering and obtaining filtrate, rectifying, controlling the vacuum degree to be 0.15 MPa, and controlling the temperature to be 152 ℃ to obtain the 3-bromo-4-fluoroacetophenone ethylene glycol.
S2, adding 10 mmol of 3-bromo-4-fluoro acetophenone ethylene glycol and 11 mmol of triisopropyl borate into acetone, dropwise adding an acetone solution containing 15 mmol of n-butyl lithium in a low-temperature reactor under nitrogen atmosphere, reacting 3, h, dropwise adding a dilute hydrochloric acid solution to adjust the pH value to 2 after the reaction, standing for 12, h, concentrating under reduced pressure to remove an organic solvent, adding ethyl acetate and water, standing for layering, extracting and separating to obtain an ethyl acetate organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, washing a crude product with a mixed solution of dichloromethane and petroleum ether, and recrystallizing with a mixed solution of methanol and water to obtain the 5-acetyl-2-fluorobenzeneboric acid.
S3, dissolving 20 mmol of 5-acetyl-2-fluorobenzeneboronic acid and 30 mmol of pinacol into tetrahydrofuran, then adding 56 mmol of magnesium sulfate, reacting 4-h, filtering to remove magnesium sulfate, concentrating under reduced pressure to remove a solvent, adding a crude product into toluene and water, and extracting and separating to obtain a toluene organic phase; then adding saturated saline, extracting and separating to obtain a toluene organic phase, adding magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, and washing with n-hexane to obtain the 5-acetyl-2-fluorobenzeneboronic acid pinacol ester.
Examples
S1, sequentially adding 20 mmol of 3-bromo-4-fluorobenzoketone, 36 mmol of triethyl orthoformate and 48 mmol of ethylene glycol into a reaction bottle, then adding a catalyst p-toluenesulfonic acid which is 1.3% of the total mass of reactants, reacting at constant temperature in a nitrogen atmosphere for 8 h, adding saturated sodium bicarbonate solution after the reaction, standing for layering, extracting and separating an upper water phase, then adding dichloromethane, standing for layering, extracting and separating a lower organic phase, adding anhydrous magnesium sulfate for drying and dehydrating, filtering, taking filtrate, rectifying, controlling the vacuum degree to be 0.1 MPa, and controlling the temperature to be 156 ℃ to obtain the 3-bromo-4-fluoroacetophenone ethylene glycol.
S2, adding 10 mmol of 3-bromo-4-fluoroacetophenone ethylene glycol and 13 mmol of tributyl borate into tetrahydrofuran, dropwise adding a tetrahydrofuran solution containing 18 mmol of n-butyllithium in a low-temperature reactor under nitrogen atmosphere, reacting 4, h, dropwise adding a dilute hydrochloric acid solution to adjust the pH value to 2 after the reaction, standing 18, h, concentrating under reduced pressure to remove an organic solvent, adding ethyl acetate and water, standing for layering, extracting and separating to obtain an ethyl acetate organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, washing a crude product with a mixed solution of dichloromethane and petroleum ether, and recrystallizing with a mixed solution of methanol and water to obtain the 5-acetyl-2-fluorobenzeneboric acid.
S3, dissolving 20 mmol of 5-acetyl-2-fluorobenzeneboronic acid and 30 mmol of pinacol into tetrahydrofuran, then adding 56 mmol of magnesium sulfate, reacting 5 h, filtering to remove magnesium sulfate, concentrating under reduced pressure to remove a solvent, adding a crude product into toluene and water, and extracting and separating to obtain a toluene organic phase; then adding saturated saline, extracting and separating to obtain a toluene organic phase, adding magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, and washing with n-hexane to obtain the 5-acetyl-2-fluorobenzeneboronic acid pinacol ester.
Examples
S1, sequentially adding 20 mmol of 3-bromo-4-fluorobenzoketone, 30 mmol of triethyl orthoformate and 48 mmol of ethylene glycol into a reaction bottle, then adding a catalyst p-toluenesulfonic acid which is 1.2% of the total mass of reactants, reacting at constant temperature in a nitrogen atmosphere for 5 h, adding saturated sodium bicarbonate solution after the reaction, standing for layering, extracting and separating an upper water phase, then adding dichloromethane, standing for layering, extracting and separating a lower organic phase, adding anhydrous magnesium sulfate for drying and dehydrating, filtering, taking filtrate, rectifying, controlling the vacuum degree to be 0.12 MPa, and controlling the temperature to be 156 ℃ to obtain the 3-bromo-4-fluoroacetophenone ethylene glycol.
S2, adding 10 mmol of 3-bromo-4-fluoroacetophenone ethylene glycol and 13 mmol of tributyl borate into tetrahydrofuran, dropwise adding a tetrahydrofuran solution containing 18 mmol of n-butyllithium in a low-temperature reactor under nitrogen atmosphere, reacting 3, h, dropwise adding a dilute hydrochloric acid solution to adjust the pH value to 1 after the reaction, standing for 12, h, concentrating under reduced pressure to remove an organic solvent, adding ethyl acetate and water, standing for layering, extracting and separating to obtain an ethyl acetate organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, washing a crude product with a mixed solution of dichloromethane and petroleum ether, and recrystallizing with a mixed solution of methanol and water to obtain the 5-acetyl-2-fluorobenzeneboric acid.
S3, dissolving 20 mmol of 5-acetyl-2-fluorobenzeneboronic acid and 24 mmol of pinacol into tetrahydrofuran, then adding 50 mmol of magnesium sulfate, reacting 6 h, filtering to remove magnesium sulfate, concentrating under reduced pressure to remove a solvent, adding a crude product into toluene and water, and extracting and separating to obtain a toluene organic phase; then adding saturated saline, extracting and separating to obtain a toluene organic phase, adding magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, and washing with n-hexane to obtain the 5-acetyl-2-fluorobenzeneboronic acid pinacol ester.

Claims (7)

1. A preparation method of 5-acetyl-2-fluorobenzeneboronic acid pinacol ester is characterized by comprising the following steps of: the preparation method comprises the following steps:
s1, sequentially adding 3-bromo-4-fluorobenzoketone, triethyl orthoformate and ethylene glycol into a reaction bottle, then adding a catalyst p-toluenesulfonic acid, reacting at constant temperature of 25-35 ℃ in a nitrogen atmosphere for 4-8 h, adding a saturated sodium bicarbonate solution after the reaction, standing for layering, extracting and separating an upper water phase, then adding dichloromethane, standing for layering, extracting and separating a lower organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering, taking filtrate, rectifying, controlling the vacuum degree to be 0.1-0.15 MPa, and controlling the temperature to be 152-156 ℃ to obtain 3-bromo-4-fluoroacetophenone ethylene glycol;
s2, adding 3-bromo-4-fluoro acetophenone glycol and a boration reagent into an organic solvent, dropwise adding a solution of n-butyllithium in a low-temperature reactor under nitrogen atmosphere, reacting 2-4 h, dropwise adding a dilute hydrochloric acid solution after the reaction to adjust the pH to 1-2, standing for 6-18 h, concentrating under reduced pressure to remove the organic solvent, adding ethyl acetate and water, standing for layering, extracting and separating to obtain an ethyl acetate organic phase, adding anhydrous magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, washing a crude product with a mixed solution of dichloromethane and petroleum ether, and recrystallizing with a mixed solution of methanol and water to obtain 5-acetyl-2-fluorobenzeneboronic acid;
s3, dissolving 5-acetyl-2-fluorobenzeneboronic acid and pinacol into tetrahydrofuran, then adding magnesium sulfate, reacting 4-8 h, filtering to remove magnesium sulfate, concentrating under reduced pressure to remove solvent, adding the crude product into toluene and water, and extracting and separating to obtain a toluene organic phase; then adding saturated saline, extracting and separating to obtain a toluene organic phase, adding magnesium sulfate for drying and removing water, filtering, concentrating the filtrate under reduced pressure, and washing with n-hexane to obtain the 5-acetyl-2-fluorobenzeneboronic acid pinacol ester.
2. The method for preparing 5-acetyl-2-fluorobenzeneboronic acid pinacol ester according to claim 1, which is characterized in that: the molar ratio of 3-bromo-4-fluorobenzone, triethyl orthoformate and ethylene glycol in S1 is 1:1.3-1.8:1.7-2.4.
3. The method for preparing 5-acetyl-2-fluorobenzeneboronic acid pinacol ester according to claim 1, which is characterized in that: the catalyst p-toluenesulfonic acid in S1 is 1-1.3% of the total mass of the reactants.
4. The method for preparing 5-acetyl-2-fluorobenzeneboronic acid pinacol ester according to claim 1, which is characterized in that: the organic solvent in S2 comprises tetrahydrofuran, 1, 4-dioxane or acetone.
5. The method for preparing 5-acetyl-2-fluorobenzeneboronic acid pinacol ester according to claim 1, which is characterized in that: the reaction mole ratio of the 3-bromo-4-fluoro acetophenone glycol, the boration reagent and the n-butyl lithium in the S2 is 1:1-1.3:1.2-1.8.
6. The method for preparing 5-acetyl-2-fluorobenzeneboronic acid pinacol ester according to claim 1, which is characterized in that: the boration agent in S2 comprises tributyl borate or triisopropyl borate.
7. The method for preparing 5-acetyl-2-fluorobenzeneboronic acid pinacol ester according to claim 1, which is characterized in that: the reaction mole ratio of the 5-acetyl-2-fluorobenzeneboronic acid, pinacol and magnesium sulfate in the S3 is 1:1-1.5:2-2.8.
CN202310285965.9A 2023-03-22 2023-03-22 Preparation method of 5-acetyl-2-fluorobenzeneboronic acid pinacol ester Pending CN116425782A (en)

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