Polysubstituted benzoic acid and a synthesis method thereof

A synthesis method and technology of benzoic acid, applied in chemical instruments and methods, preparation of sulfonic acid amide, preparation of organic compounds, etc., can solve problems such as increased operation complexity and unfavorable product purification, and achieve cheap preparation of raw materials and high yield of target products The effect of high efficiency and wide applicability

Active Publication Date: 2019-06-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Traditional multi-substituted benzoic acid uses Friedel-Crafts reaction to introduce alkyl groups, or needs to use metal reagents, such as boric acid, Grignard reagents, etc. to introduce alkyl or aryl groups into benzene rings. These methods are almost all It is necessary to protect the carboxyl group of benzoic acid in advance, which increases the cumbersomeness of the operation, and will introduce more other substances into the system, or produce a large number of by-products, which is not conducive to the purification of the product, and directly uses the carboxyl group as a guide Group, the introduction of different groups in the ortho position will greatly simplify the synthesis steps and improve the efficiency

Method used

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  • Polysubstituted benzoic acid and a synthesis method thereof
  • Polysubstituted benzoic acid and a synthesis method thereof
  • Polysubstituted benzoic acid and a synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032]

[0033] In a 25mL reaction tube, m-toluic acid 2a (0.2mmol), palladium acetate (10mol%), aziridine 3a (0.4mmol), potassium acetate (0.2mmol), N-acetylglycine ( 20mol%) and 0.5mL of hexafluoroisopropanol, stirred at 80°C for 24 hours. After cooling to room temperature, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=10:1) to obtain the target product 1a (58 mg, yield 70%). The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0035]

[0036] In a 25mL reaction tube, under air, add polysubstituted benzoic acid 1a (0.2mmol), dehydroabietylamine 4 (0.22mmol), DCC (0.24mmol), HOBt (0.24mmol) and 2.0Ml dichloromethane, at room temperature Stir for 24 hours. After cooling to room temperature, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=10:1) to obtain the target product 5 (110 mg, yield 81%). The target product was confirmed by NMR and high-resolution mass spectrometry.

[0037] Compound 1a NMR assignment:

[0038] Multi-substituted benzoic acid derivatives (1a), pale yellow liquid. 1 H NMR (400MHz, CDCl 3 )δ7.97(s,1H,aromatic CH),7.65(d,2H,aromatic CH),7.38(m,4H,aromatic CH),7.24(m,5H,aromatic CH),4.53(m,2H,aromatic CHand NH),3.95(m,1H,CH 2 ),3.70(m,1H,CH 2 ),2,41(s,6H,CH 3 ). 13 C{ 1 H) NMR (100MHz, CDCl 3 ), 50.6 (CH 2 ), 49.2(CH), 21.2and 21.1(CH 3 ). 23 h ...

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Abstract

The invention discloses a synthetic method of polysubstituted benzoic acid. Benzoic acid which is simple and easy to obtain and aziridine which is easy to prepare are used as raw materials, synthesisof polysubstituted benzoic acid is achieved in one step, and the obtained polysubstituted benzoic acid can be further converted into a functional product. The method has the advantages of easily available raw materials, simple operation, mild synthesis reaction conditions, high reaction efficiency, and diversity of functional groups.

Description

technical field [0001] The invention discloses a method for synthesizing polysubstituted benzoic acid. Starting from benzoic acid and aziridine, Pd(OAc) 2 As a catalyst, under heating conditions, one-step generation of multi-substituted benzoic acid. [0002] Compared with the reported synthesis method of multi-substituted benzoic acid, the present invention has easy-to-obtain raw materials, simple operation, mild synthesis reaction conditions, high efficiency, 50%-90% yield, and good functional group diversity. [0003] The carboxyl group and the sulfonamide group in the multi-substituted benzoic acid skeleton structure synthesized by the invention are groups that can be further functionalized, and can be used as intermediates in the structure of medicines and chemical products. Background technique [0004] Benzoic acid and its derivatives are widely found in natural products and bioactive molecules, and can be converted into a series of important organic intermediates, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/19C07C311/16C07C303/40C07C303/44
Inventor 余正坤娄江
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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