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A kind of synthetic method of biphenyl derivatives

A synthesis method and technology of derivatives, applied in the field of synthesizing biphenyl derivatives, achieving the effects of environmental friendliness, simple and easy-to-obtain reaction raw materials, and simple operation

Active Publication Date: 2020-07-28
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the substrates are limited to aromatic carboxylic acids with strong electron-withdrawing ortho-positions of the carboxyl group, and the products are all ortho-substituted biphenyl derivatives

Method used

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  • A kind of synthetic method of biphenyl derivatives
  • A kind of synthetic method of biphenyl derivatives
  • A kind of synthetic method of biphenyl derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Preparation of 3,3',5,5'-tetramethylbiphenyl with the following structural formula

[0016]

[0017] Add 0.0300g (0.2mmol) 2,4-dimethylbenzoic acid, 0.0045g (0.02mmol) palladium acetate, 0.0689g (0.25mmol) silver carbonate, 0.0087g (0.05mmol) hydrogen phosphate to a 10mL pressure-resistant reaction tube Dipotassium, 0.6mL ethylene glycol dimethyl ether, under the airtight condition protected by argon, stirred and reacted at 150°C for 12 hours. Separated by layer chromatography to obtain 3,3',5,5'-tetramethylbiphenyl, the yield is 60%, and the structural characterization data are as follows:

[0018] 1 H NMR (400MHz, CDCl 3 ): δ[ppm]=7.19(s, 4H), 6.97(s, 2H), 2.37(s, 12H);

[0019] 13 C NMR (100MHz, CDCl 3 ): δ [ppm] = 141.5, 138.1, 128.7, 125.1, 21.4;

[0020] GCMS (CI) m / z: C 16 h 18 [M] The theoretical value is 210.14, and the measured value is 210.10.

Embodiment 2

[0022] Preparation of 3,3'-dimethyl-5,5'-dichlorobiphenyl with the following structural formula

[0023]

[0024] In Example 1, the 2,4-dimethylbenzoic acid used was replaced with equimolar 2-methyl-4-chlorobenzoic acid, and the other steps were the same as in Example 1 to obtain 3,3'-dimethyl -5,5'-dichlorobiphenyl, the yield is 50%, and the structural characterization data are as follows:

[0025] 1 H NMR (400MHz, CDCl 3 ): δ[ppm]=7.33(s, 2H), 7.23(s, 2H), 7.16(s, 2H), 2.39(s, 6H);

[0026] 13 C NMR (100MHz, CDCl 3 ): δ [ppm] = 141.6, 140.2, 134.4, 128.4, 126.1, 124.3, 21.3;

[0027] GCMS (CI) m / z: C 14 h 12 Cl 2 [M] The theoretical value is 250.03, and the measured value is 250.00.

Embodiment 3

[0029] Prepare the following structural formula 3,3'-dimethoxybiphenyl

[0030]

[0031] In Example 1, the 2,4-dimethylbenzoic acid used was replaced with equimolar o-methoxybenzoic acid, and the other steps were the same as in Example 1 to obtain 3,3'-dimethoxybiphenyl, Its yield is 25%, and the structural characterization data are as follows:

[0032] 1 H NMR (600MHz, CDCl 3 ):δ[ppm]=7.35(t,J=7.9Hz,2H),7.18(d,J=7.6Hz,2H),7.12(s,2H),6.90(d,J=8.2Hz,2H), 3.87(s,6H);

[0033] 13 C NMR (150MHz, CDCl 3 ): δ [ppm] = 159.9, 142.6, 129.7, 119.7, 112.9, 112.8, 55.3;

[0034] GCMS (CI) m / z: C 14 h 14 o 2 [M] The theoretical value is 214.10, and the measured value is 214.05.

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Abstract

The invention discloses a synthesis method of biphenyl derivatives. According to the method, transition metal palladium is taken as a catalyst, aromatic carboxylic acid is subjected to a carboxyl-vicinal crossed dehydrogenate coupling and decarboxylic reaction, and a series of biphenyl derivatives are synthesized in one step simply, conveniently and efficiently. The synthesis method has the advantages that raw materials are simple and easy to obtain, operation is simple, environment-friendliness is realized and the like.

Description

technical field [0001] The present invention relates to a synthesis method of biphenyl derivatives, in particular to a simple and efficient one-step synthesis method using transition metals as catalysts through carboxyl ortho-cross dehydrogenation coupling and decarboxylation reactions between aromatic carboxylic acids A method for biphenyl derivatives. Background technique [0002] Biphenyl compounds are important skeletons of many natural products, bioactive substances, agricultural chemicals, dyes, ligands and functional materials, and have a wide range of applications in the fields of dyes, drugs, semiconductors and liquid crystal materials. [0003] Organometallic-catalyzed cross-coupling reactions are an important method for the synthesis of biphenyl compounds, such as the Suzuki-Miyaura reaction of halogenated hydrocarbons and organoboron compounds (Chin.J.Org.Chem.2014,34,65-80; Chin .J.Org.Chem.2014,34,1919-1940), Stille reaction of halogenated aromatic hydrocarbon...

Claims

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Application Information

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IPC IPC(8): C07C1/20C07C15/14C07C17/26C07C17/263C07C25/18C07C41/30C07C41/18C07C43/205
CPCC07C1/20C07C17/26C07C17/263C07C41/18C07C41/30C07C2531/22C07C15/14C07C25/18C07C43/205C07C43/2055Y02P30/20Y02P30/40
Inventor 石先莹蒲帆刘忠文
Owner SHAANXI NORMAL UNIV
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