CN116715576A - Method for synthesizing alpha-bromoaryl acetic acid compound - Google Patents

Method for synthesizing alpha-bromoaryl acetic acid compound Download PDF

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Publication number
CN116715576A
CN116715576A CN202310608801.5A CN202310608801A CN116715576A CN 116715576 A CN116715576 A CN 116715576A CN 202310608801 A CN202310608801 A CN 202310608801A CN 116715576 A CN116715576 A CN 116715576A
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reaction
preparation
acetic acid
bromoaryl
aryl
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胡海鹏
赵柳英
王贝宁
吴鑫
蒋之语
陈萍萍
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Sichuan Agricultural University
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Sichuan Agricultural University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Engineering & Computer Science (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a method for synthesizing alpha-bromoaryl acetic acid compounds based on aryl acetic acid compounds, belonging to the field of organic chemistry. The method takes aryl acetic acid compounds and bromine sources as substrates, and synthesizes a series of alpha-bromoaryl acetic acid compounds through two-component reaction under the conditions of catalyst, alkalinity and 40 ℃.

Description

Method for synthesizing alpha-bromoaryl acetic acid compound
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a method for synthesizing alpha-bromoaryl acetic acid compounds based on aryl acetic acid compounds.
Background
Alpha-bromo carboxylic acids are key building blocks for many bioactive substances and are also synthetic intermediates for a variety of drug molecules. In the field of pharmaceutical synthesis, α -bromocarboxylic acid can be converted into anti-inflammatory drugs such as ibuprofen, naproxen, flurbiprofen, etc. by a simple derivatization reaction (angelw, chem, int, ed. 2019, 58, 11355). In addition, flurbiprofen (otolyng. Head. Neg. 2016, 155, 166), a drug for the clinical treatment of postoperative pain, can also be synthesized by α -bromocarboxylic acid.
Because of the p-pi conjugated effect of carboxyl in carboxylic acid molecule, the electropositivity of carboxyl carbon is weakened, and the synthesis of alpha-bromo carboxylic acid compound by a universal method is difficult. In this context, existing methods for synthesizing α -bromocarboxylic acids are as follows: synthesizing alpha-bromocarboxylic acid (Ber, dtsch, chem, ges, 1881, 14, 891.) by substituting acetic acid compounds and bromine simple substance under the action of catalytic amount of phosphorus tribromide; the synthesis of alpha-bromocarboxylic acid by direct heat refluxing of alpha-chlorocarboxylic acid with elemental bromine (j. Hetercycl. Chem. 2001, 38, 997). The synthesis method has the advantages of intense reaction and high synthesis difficulty. Therefore, the invention has important research value in an economical and practical synthesis method of the alpha-bromo-carboxylic acid.
Disclosure of Invention
The alpha-bromoaryl acetic acid compound synthesized by the invention is not only a core skeleton of a plurality of bioactive molecules, but also an important synthon in organic synthesis. Therefore, the type of the novel alpha-bromoaryl acetic acid compound is expanded, and the realization of the efficient synthesis of bioactive molecules has important research significance.
In order to achieve the above object, the present invention provides a method for synthesizing an α -bromoaryl acetic acid compound having a structure represented by formula i:
。
wherein Ar is selected from any one of aryl, naphthyl, benzyl, substituted benzyl and substituted aryl.
R 1 Selected from any one of saturated alkyl groups and hydrogen atoms.
The substituent of the substituted aryl and the substituted benzyl is any one of saturated alkyl, halogen atom, cyano, alkoxy, aryl and trifluoro sulfonic acid.
The method comprises the following steps: under the protection of nitrogen, sequentially adding 2-phenylacetic acid, a bromine source, a catalyst, alkali and a solvent into a drying reactor, and stirring at a certain temperature until the reaction is completed to obtain an alpha-bromoaryl acetic acid compound, wherein the chemical process is shown as a reaction formula II:
。
the [ Br ] is selected from any different one of bromine simple substance, dibromohydantoin, tribromide pyridine, pentafluorobromobenzene, N-bromosuccinimide, N-bromoo-sulfonylbenzene imide and dibromomeldonium acid.
The alkali is selected from any different one of 4-dimethylaminopyridine, pyridine, tetramethylguanidine, 1, 8-diazabicyclo (5.4.0) undec-7-ene and sodium carbonate.
The solvent is selected from any different one of toluene, acetonitrile, diethyl ether, dimethyl ether and tetrahydrofuran.
The catalyst is selected from any one of phenylboronic acid, boric acid, pentafluorophenylboronic acid, dipyrniol diboron and tetraacetyl diboronate.
The molar ratio of the aryl acetic acid compound to the bromine source to the Lewis base to the catalyst is 1.0: (1.0-1.5): (2.0-2.5): 0.2.
the reaction time is 24-72h.
The reaction temperature is 25-100 ℃.
After the reaction, the esterification operation is carried out, and the column chromatography separation is carried out by using the mixed solvent of petroleum ether and ethyl acetate.
The beneficial effects of the invention are as follows: the invention provides a method for synthesizing an alpha-bromoaryl acetic acid compound, which is scientific and reasonable and has the advantages of high yield, wide substrate application range, simple operation, convenient post-treatment and the like.
Drawings
FIG. 1 is a schematic diagram of example 1 1 H NMR spectrum; FIG. 2 is a schematic diagram of example 1 13 C NMR spectrum; FIG. 3 is a schematic diagram of example 1 19 F NMR spectrum.
FIG. 4 is a schematic diagram of example 2 1 H NMR spectrum; FIG. 5 is a schematic diagram of example 2 13 C NMR spectrum.
FIG. 6 is a diagram of example 3 1 H NMR spectrum; FIG. 7 is a diagram of example 3 13 C NMR spectrum.
FIG. 8 is a schematic diagram of example 4 1 H NMR spectrum; FIG. 9 is a diagram of example 4 13 C NMR spectrum.
FIG. 10 is a diagram of example 5 1 H NMR spectrum; FIG. 11 is a diagram of example 5 13 C NMR spectrum.
FIG. 12 is a schematic illustration of example 6 1 H NMR spectrum; FIG. 13 is a schematic illustration of example 6 13 C NMR spectrum.
FIG. 14 is a schematic diagram of example 7 1 H NMR spectrum; FIG. 15 is a schematic view of example 7 13 C NMR spectrum.
FIG. 16 is a diagram of example 8 1 H NMR spectrum; FIG. 17 is a diagram of example 8 13 C NMR spectrum.
Detailed Description
The method of the present invention is described herein by way of specific examples, but the present invention is not limited thereto, and any modification, equivalent substitution, improvement, etc. within the scope of the technical idea of the present invention should be included in the scope of the present invention.
Example 1:
the reaction equation is as follows:
。
under nitrogen, compound 1a (0.1 mmol), 2a (0.15 mmol) and tetraacetyl diboronate (20 mol%) were added to a dry reactor and 1, 8-diazabicyclo (5.4.0) undec-7-ene (2.0 eq) and ethylene glycol dimethyl ether (1.0 mL) were added and stirred at 25 ℃ until the reaction was complete. After completion of the reaction, the reaction solution was concentrated by a rotary evaporator to obtain 3a. In order to facilitate the subsequent separation and purification, the product is subjected to esterification operation. Compound 3a (0.1 mmol) was added to the dried reactor and thionyl chloride (2.0 eq) and methanol (1.0 mL) were added and stirred at 80 ℃ until the reaction was complete. After the reaction was completed, the mixture was separated by column chromatography using petroleum ether and ethyl acetate 80:1 to give pure 3aa in 51% yield.
The nuclear magnetic data of 3aa are as follows:
1 H NMR (600 MHz, CDCl 3 ) δ 7.49 (m, 2H), 7.13 – 7.00 (m, 2H), 5.34 (s, 1H), 3.78 (s, 3H).。
13 C NMR (151 MHz, CDCl 3 ) δ 168.73 , 131.64 , 129.96 , 115.85 , 58.10 , 53.43 .。
19 F NMR (565 MHz, CDCl 3 ) δ -111.67.。
example 2:
the reaction equation is as follows:
。
compound 1b (0.1 mmol), 2a (0.15 mmol) and tetraacetyl diboronate (20 mol%) were added to a dry reactor under nitrogen, followed by 1, 8-diazabicyclo (5.4.0) undec-7-ene (2.0 eq) and ethylene glycol dimethyl ether (1.0 mL) and stirred at 25℃until the reaction was completed. After completion of the reaction, the reaction solution was concentrated by a rotary evaporator to obtain 3b. In order to facilitate the subsequent separation and purification, the product is subjected to esterification operation. Compound 3b (0.1 mmol) was added to the dried reactor and thionyl chloride (2.0 eq) and methanol (1.0 mL) were added and stirred at 80 ℃ until the reaction was complete. After completion of the reaction, the mixture was separated by column chromatography using petroleum ether and ethyl acetate at 80:1 to give pure 3ba in 54% yield.
The nuclear magnetic data of 3ba are as follows:
1 H NMR (600 MHz, CDCl 3 ) δ 7.44 (d, J = 8.5 Hz, 2H), 7.36 (d, J = 8.5 Hz, 2H), 5.33 (s, 1H), 3.78 (s, 3H).。
13 C NMR (151 MHz, CDCl 3 ) δ 168.53, 135.42, 134.21, 129.36, 129.12, 58.10, 53.48.。
example 3:
the reaction equation is as follows:
。
compound 1c (0.1 mmol), 2a (0.15 mmol) and tetraacetyl diboronate (20 mol%) were added to a dry reactor under nitrogen, followed by 1, 8-diazabicyclo (5.4.0) undec-7-ene (2.0 eq) and ethylene glycol dimethyl ether (1.0 mL) and stirred at 25℃until the reaction was completed. After completion of the reaction, the reaction solution was concentrated by a rotary evaporator to obtain 3c. In order to facilitate the subsequent separation and purification, the product is subjected to esterification operation. Compound 3c (0.1 mmol) was added to the dried reactor and thionyl chloride (2.0 eq) and methanol (1.0 mL) were added and stirred at 80 ℃ until the reaction was complete. After the reaction was completed, the mixture was separated by column chromatography using petroleum ether and ethyl acetate at 80:1 to give pure 3ca in 49% yield.
The nuclear magnetic data of 3ca are as follows:
1 H NMR (600 MHz, CDCl 3 ) δ 7.54 – 7.50 (m, 2H), 7.40 – 7.35 (m, 2H), 5.31 (s, 1H), 3.78 (s, 3H).。
13 C NMR (151 MHz, CDCl 3 ) δ 168.45, 134.72, 132.08, 129.63, 123.62, 58.15, 53.49.。
example 4:
the reaction equation is as follows:
。
compound 1d (0.1 mmol), 2a (0.15 mmol) and tetraacetyl diboronate (20 mol%) were added to a dry reactor under nitrogen, followed by 1, 8-diazabicyclo (5.4.0) undec-7-ene (2.0 eq) and ethylene glycol dimethyl ether (1.0 mL) and stirred at 25℃until the reaction was completed. After completion of the reaction, the reaction solution was concentrated by a rotary evaporator to obtain 3d. In order to facilitate the subsequent separation and purification, the product is subjected to esterification operation. Compound 3d (0.1 mmol) was added to the dried reactor and thionyl chloride (2.0 eq) and methanol (1.0 mL) were added and stirred at 80 ℃ until the reaction was complete. After the reaction was completed, the mixture was separated by column chromatography using petroleum ether and ethyl acetate at 80:1 to give pure 3da in 46% yield.
The nuclear magnetic data of 3da are as follows:
1 H NMR (600 MHz, CDCl 3 ) δ 7.75 – 7.70 (m, 2H), 7.26 – 7.21 (m, 2H), 5.29 (s, 1H), 3.77 (s, 3H).。
13 C NMR (151 MHz, CDCl 3 ) δ 168.41, 138.03, 135.36, 129.72, 95.41, 58.26, 53.48.。
example 5:
the reaction equation is as follows:
。
compound 1e (0.1 mmol), 2a (0.15 mmol) and tetraacetyl diboronate (20 mol%) were added to a dry reactor under nitrogen protection, followed by 1, 8-diazabicyclo (5.4.0) undec-7-ene (2.0 eq) and ethylene glycol dimethyl ether (1.0 mL) and stirred at 25 ℃ until the reaction was completed. After completion of the reaction, the reaction solution was concentrated by a rotary evaporator to obtain 3e. In order to facilitate the subsequent separation and purification, the product is subjected to esterification operation. Compound 3e (0.1 mmol) was added to the dried reactor and thionyl chloride (2.0 eq) and methanol (1.0 mL) were added and stirred at 80 ℃ until the reaction was complete. After the reaction was completed, the mixture was separated by column chromatography using petroleum ether and ethyl acetate at 80:1 to give pure 3ea in 45% yield.
The nuclear magnetic data of 3ea are as follows:
1 H NMR (600 MHz, CDCl 3 ) δ 7.34 – 7.25 (m, 2H), 7.11 (d, J = 7.9 Hz, 2H), 5.26 (s, 1H), 3.69 (s, 3H), 2.28 (s, 3H).。
13 C NMR (151 MHz, CDCl 3 ) δ 169.01, 139.44, 132.84, 129.60, 127.87, 58.91, 53.30, 21.23.。
example 6:
the reaction equation is as follows:
。
under nitrogen, compound 1f (0.1 mmol), 2a (0.15 mmol) and tetraacetyl diboronate (20 mol%) were added to a dry reactor and 1, 8-diazabicyclo (5.4.0) undec-7-ene (2.0 eq) and ethylene glycol dimethyl ether (1.0 mL) were added and stirred at 25 ℃ until the reaction was complete. After completion of the reaction, the reaction solution was concentrated by a rotary evaporator to obtain 3f. In order to facilitate the subsequent separation and purification, the product is subjected to esterification operation. Compound 3f (0.1 mmol) was added to the dried reactor and thionyl chloride (2.0 eq) and methanol (1.0 mL) were added and stirred at 80 ℃ until the reaction was complete. After the reaction was completed, the mixture was separated by column chromatography using petroleum ether and ethyl acetate at 80:1 to give pure 3fa in 37% yield.
The nuclear magnetic data of 3fa are as follows:
1 H NMR (600 MHz, CDCl 3 ) δ 7.64 (m, 4H), 5.40 (s, 1H), 3.79 (s, 3H).。
13 C NMR (151 MHz, CDCl 3 ) δ 168.26, 139.46, 131.80, 131.58, 131.37, 131.15, 128.43, 125.92, 125.90, 125.87, 125.85, 124.63, 122.83, 58.01, 53.60.。
example 7:
the reaction equation is as follows:
。
1g (0.1 mmol), 2a (0.15 mmol) and tetraacetyl diboronate (20 mol%) of the compound are introduced into a dry reactor under nitrogen, 1, 8-diazabicyclo (5.4.0) undec-7-ene (2.0 eq) and ethylene glycol dimethyl ether (1.0 mL) are added and stirred at 25℃until the reaction is completed. After completion of the reaction, the reaction solution was concentrated by a rotary evaporator to obtain 3g. In order to facilitate the subsequent separation and purification, the product is subjected to esterification operation. 3g (0.1 mmol) of the compound was charged into a dry reactor, and thionyl chloride (2.0 eq) and methanol (1.0 mL) were added thereto and stirred at 80℃until the reaction was completed. After completion of the reaction, the mixture was separated by column chromatography using petroleum ether and ethyl acetate at 80:1 to give pure 3ga in 59% yield.
The nuclear magnetic data at 3ga were as follows:
1 H NMR (400 MHz, CDCl 3 ) δ 7.58 (m, 1H), 7.49 (m, 1H), 7.37 (m, 2H), 7.29 – 7.08 (m, 6H), 7.04 (m, 1H), 5.91 (d, J = 2.5 Hz, 1H), 5.32 – 5.17 (m, 4H), 3.71 (d, J = 2.6 Hz, 3H).。
13 C NMR (151 MHz, CDCl 3 ) δ 168.98, 151.48, 145.52, 135.11, 135.07, 134.10, 133.00, 132.82, 130.85, 129.85, 129.76, 129.45, 129.35, 129.31, 129.21, 129.16, 127.03, 126.90, 124.89, 124.84, 122.27, 121.21, 114.83, 114.78, 72.15, 68.15, 53.32, 53.17, 40.78.。
example 8:
the reaction equation is as follows:
。
under nitrogen, the compound 1h (0.1 mmol), 2a (0.15 mmol), tetraacetyl diboronate (20 mol%) was added to the dry reactor, followed by 1, 8-diazabicyclo (5.4.0) undec-7-ene (2.0 eq) and ethylene glycol dimethyl ether (1.0 mL) and stirred at 25 ℃ until the reaction was completed. After completion of the reaction, the reaction solution was concentrated by a rotary evaporator for 3 hours. In order to facilitate the subsequent separation and purification, the product is subjected to esterification operation. Compound 3h (0.1 mmol) was added to the dried reactor and thionyl chloride (2.0 eq) and methanol (1.0 mL) were added and stirred at 80 ℃ to the end of the reaction. After the reaction was completed, the mixture was separated by column chromatography using petroleum ether and ethyl acetate at 80:1 to give pure 3ha in 61% yield.
The nuclear magnetic data of 3ha are as follows:
1 H NMR (600 MHz, CDCl 3 ) δ 7.25 (d, J = 1.9 Hz, 1H), 7.20 (m, 1H), 7.13 (d, J = 7.9 Hz, 1H), 5.31 (s, 1H), 3.76 (s, 3H), 2.26 (d, J = 7.4 Hz, 6H).。
13 C NMR (151 MHz, CDCl 3 ) δ 169.09, 138.17, 137.37, 133.18, 130.13, 129.03, 125.37, 59.03, 53.30, 19.80, 19.59.。
from the above examples, it can be seen that the various and efficient syntheses of α -bromoaryl acetic acid compounds are possible according to the present invention.

Claims (12)

1. A synthesis method of an alpha-bromoaryl acetic acid compound comprises the following steps:
2. wherein Ar is selected from any one of aryl, naphthyl, benzyl, substituted benzyl and substituted aryl;
R 1 selected from any one of saturated alkyl groups and hydrogen atoms.
3. The substituent of the substituted aryl and the substituted benzyl is any one of saturated alkyl, halogen atom, cyano, alkoxy, aryl and trifluoro sulfonic acid.
4. The method comprises the following steps: under the protection of nitrogen, sequentially adding 2-phenylacetic acid, a bromine source, a catalyst, alkali and a solvent into a drying reactor, stirring at a certain temperature until the reaction is completed, and separating by column chromatography to obtain the alpha-bromoaryl acetic acid compound, wherein the chemical process is shown in a reaction formula II:
5. the preparation method according to claim 1, wherein [ Br ] is any different one selected from the group consisting of elemental bromine, dibromohydantoin, pyridine tribromide, pentafluorobromobenzene, N-bromosuccinimide, N-bromophthalimide, dibromomeldonium acid.
6. The preparation method according to claim 1, wherein the base is any different one selected from 4-dimethylaminopyridine, pyridine, tetramethylguanidine, 1, 8-diazabicyclo (5.4.0) undec-7-ene, and sodium carbonate.
7. The preparation method according to claim 1, wherein the solvent is selected from any different one of toluene, acetonitrile, diethyl ether, dimethyl ether, and tetrahydrofuran.
8. The preparation method according to claim 1, wherein the catalyst is any one selected from phenylboronic acid, boric acid, pentafluorophenylboronic acid, dipinacol diboron, and tetraacetyldiboronate.
9. The preparation method according to claim 1, wherein the molar ratio of the aryl acetic acid compound, [ Br ], the Lewis base and the catalyst is 1.0: (1.0-1.5): (2.0-2.5): 0.2.
10. the preparation method according to claim 1, wherein the reaction time is 24 to 72 hours.
11. The preparation method according to claim 1, wherein the reaction temperature is 25 to 100 ℃.
12. The process according to claim 1, wherein the esterification is carried out after the completion of the reaction, and the column chromatography is carried out using a mixed solvent of petroleum ether and ethyl acetate.
CN202310608801.5A 2023-05-29 2023-05-29 Method for synthesizing alpha-bromoaryl acetic acid compound Pending CN116715576A (en)

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