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A kind of bi/heteroaromatic compound and preparation method thereof

A compound and heteroaromatic technology applied in the field of organic chemical synthesis to achieve good promotion prospects, short reaction time, and environmental friendliness

Active Publication Date: 2022-04-26
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, mechanical grinding methods have broad prospects in inducing chemical bond breakage in polymers and synergizing with chemical catalysts to promote free radical reactions. However, there are no reports that directly use mechanical force to stimulate chemical bond breakage in small molecular compounds to participate in free radical reactions.

Method used

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  • A kind of bi/heteroaromatic compound and preparation method thereof
  • A kind of bi/heteroaromatic compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0033] Example 1 Preparation of 4'-chloro-2,4,6-trimethoxy-1,1'-biphenyl

[0034] Add p-chlorobenzene tetrafluoroborate diazonium salt (113.2 mg, 0.5 mmol), 1,3,5-trimethoxybenzene (336.4 mg, 2.0 mmol), sodium chloride (146.3 mg , 2.5 mmol), and then add a stainless steel ball with a diameter of 12 mm, tighten the grinding jar, put it into a vibrating grinder, and grind at a frequency of 30 Hz for 30 minutes. After the reaction, all the reaction mixture was poured out from the grinding tank, the stainless steel ball was taken out, and the solid powder was directly separated by column chromatography with an eluent of petroleum ether and ethyl acetate (volume ratio of 100:1), and the obtained product contained The eluate of the target compound was concentrated under reduced pressure to obtain 4'-chloro-2,4,6-trimethoxy-1,1'-biphenyl, 76.6 mg, yield 55%.

[0035] White solid, melting point: 90.3–93.3 ℃, 1H NMR (400 MHz, Chloroform-d) δ 7.36–7.33(m, 2H), 7.29–7.25 (m, 2H, subtrac...

Embodiment 2

[0036] Example 2 Preparation of 4'-chloro-2,4,6-trimethoxy-1,1'-biphenyl

[0037]Add p-chlorobenzene tetrafluoroborate diazonium salt (113.2 mg, 0.5 mmol), 1,3,5-trimethoxybenzene (336.4 mg, 2.0 mmol), sodium bromide (257.3 mg , 2.5 mmol), and then add a stainless steel ball with a diameter of 10 mm, tighten the grinding jar, put it into a vibrating grinder, and grind at a frequency of 30 Hz for 30 minutes. After the reaction, all the reaction mixture was poured out from the grinding tank, the stainless steel ball was taken out, and the solid powder was directly separated by column chromatography with an eluent of petroleum ether and ethyl acetate (volume ratio of 100:1), and the obtained product contained The eluate of the target compound was concentrated under reduced pressure to obtain 4'-chloro-2,4,6-trimethoxy-1,1'-biphenyl, 71.1 mg, yield 51%. Physical property data is with embodiment 1.

Embodiment 3

[0038] Example 3 Preparation of 4'-chloro-2,4,6-trimethoxy-1,1'-biphenyl

[0039] Add p-chlorobenzene tetrafluoroborate diazonium salt (113.2 mg, 0.5 mmol), 1,3,5-trimethoxybenzene (336.4 mg, 2.0 mmol), potassium chloride (186.3 mg , 2.5 mmol), and then add 2 stainless steel balls with a diameter of 10 mm, tighten the grinding jar, put it into a vibratory grinder, and grind at a frequency of 25 Hz for 60 minutes. After the reaction, all the reaction mixture was poured out from the grinding tank, the stainless steel ball was taken out, and the solid powder was directly separated by column chromatography with an eluent of petroleum ether and ethyl acetate (volume ratio of 100:1), and the obtained product contained The eluate of the target compound was concentrated under reduced pressure to obtain 4'-chloro-2,4,6-trimethoxy-1,1'-biphenyl, 75.2 mg, yield 54%. Physical property data is with embodiment 1.

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Abstract

The invention discloses a bi / heteroaromatic compound and a preparation method thereof. The structural formula of the bi / heteroaromatic compound is shown in formula 3; The nitrogen salt compound and the heteroaromatic compound shown in Formula 2 are used as raw materials, and under the action of grinding aids, the free radical C-H arylation reaction is carried out by mechanical grinding to obtain the bi / heteroaromatic compound shown in Formula 3 Compounds; the present invention adopts mechanical grinding for the first time to directly induce the cleavage of the C-N bond of aryltetrafluoroborate diazonium salt, and carry out free radical C-H arylation reaction to prepare bi / heteroaromatic compounds quickly and efficiently. It has significant advantages such as no solvent, simple operation, clean and cheap system, fast and efficient reaction.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a bi / heteroaromatic compound and a preparation method thereof, which is a solvent-free mechanical grinding synthesis method through direct induction of free radical reaction by mechanical force. Background technique [0002] Bi / heteroaromatic compounds have a variety of important uses in the fields of biomedicine and fine chemicals, and are widely found in natural products and pharmaceutical active molecules. For example, natural products honokiol, sea papaverine, etc.; clinically widely used for anti-tumor (ibrutinib and imatinib), antipyretic and analgesic (fenbufen), blood pressure lowering (losartan ), Uric acid-lowering (Febuxostat) and other fields. Therefore, a simple, versatile, and sustainable strategy to access bi / heteroarenes remains in high demand in the field of chemical synthesis. [0003] There are usually three methods for the preparation of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/30C07C43/225C07D333/12C07D213/26C07D333/50C07D209/12C07D231/56
CPCC07C41/30C07D333/12C07D213/26C07D333/50C07D209/12C07D231/56C07C43/225
Inventor 俞静波杨鑫杰王浩苏为科
Owner ZHEJIANG UNIV OF TECH
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