Biaryl compound as well as preparation method and application thereof

A compound, biaryl technology, applied in the field of biaryl compounds and their preparation, to achieve the effects of high economic benefits, simple post-treatment, and mild reaction conditions

Active Publication Date: 2021-09-17
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The primary purpose of the present invention is to provide a method for preparing biaryl compounds, aiming to solve various deficiencies in the existing preparation process of biaryl compounds

Method used

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  • Biaryl compound as well as preparation method and application thereof
  • Biaryl compound as well as preparation method and application thereof
  • Biaryl compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048](1) Weigh magnesium chips (72.9mg, 3mmol, 3equiv.) and lithium chloride (84.8mg, 2mmol, 2equiv.) and add to the schlenk seal tube. Then under reduced pressure, the mixture of magnesium chips and lithium chloride was heated with an electric heat gun (320° C., 3 minutes).

[0049] (2) After the mixture was cooled to room temperature, 3 mL of ultra-dry tetrahydrofuran was added thereto, and then the tube was sealed and replaced with nitrogen three times. Subsequently, phenyl trimethyl quaternary ammonium iodide (263.1 mg, 1 mmol, 1 equiv.), bistriphenylphosphine palladium dichloride (35.1 mg, 0.05 mmol, 5 mol%), 4-methyl Oxybromobenzene (374.1mg, 2mmol, 2equiv.) and N,N,N',N'-tetramethylethylenediamine (232.4mg, 2mmol, 2equiv.), the mixture was stirred at room temperature for 12 hours.

[0050] (3) Subsequent quenching with saturated ammonium chloride solution and extraction with ethyl acetate. After the extract was washed with saturated brine and dried over anhydrous sod...

Embodiment 2～32

[0054] Embodiments 2 to 32 are basically the same as the above-mentioned embodiment 1, except that in step (1), the aryl quaternary ammonium salt and the aryl bromide are different, as shown in Table 1 below:

[0055] Table 1 Examples 2-32

[0056]

[0057]

[0058] The products in the above table are randomly selected for characterization, wherein, image 3 is the hydrogen spectrum of product 4 (4-benzyloxybiphenyl), Figure 4 It is the carbon spectrum of product 4 (4-benzyloxybiphenyl); Figure 5 is the hydrogen spectrum of product 6 (3-methoxybiphenyl), Image 6 It is the carbon spectrum of product 6 (3-methoxybiphenyl); Figure 7 is the hydrogen spectrum of product 10 (4-dimethylaminobiphenyl), Figure 8 Is the carbon spectrum of product 10 (4-dimethylaminobiphenyl); Figure 9 is the hydrogen spectrum of product 26 (4-fluoro-4'-methoxy-1,1'-biphenyl), Figure 10 is the fluorine spectrum of product 26 (4-fluoro-4'-methoxy-1,1'-biphenyl), Figure 11 is the carbo...

Embodiment 33～43

[0060] Embodiments 33 to 43 are basically the same as the above-mentioned embodiment 1, except that in step (1), the catalyst, solvent, temperature (°C), and time (h) are different, as shown in Table 2 below:

[0061] Table 2

[0062] Example number catalyst solvent temperature(℃) time (h) Yield(%) 33 Bistriphenylphosphine palladium dichloride N,N-Dimethylformamide 25 12 0 34 Bistriphenylphosphine palladium dichloride DMSO 25 12 0 35 Bistriphenylphosphine palladium dichloride N,N-Dimethylacetamide 25 12 0 36 Bistriphenylphosphine palladium dichloride Acetonitrile 25 12 0 37 Bistriphenylphosphine palladium dichloride 1,4-dioxane 25 12 0 38 Ferric chloride Tetrahydrofuran 25 12 <5

[0063] As can be seen from Table 2, under the same reaction conditions, using bistriphenylphosphine palladium dichloride as a catalyst for the reaction, in N, N-dimethylformamide, DMSO, N, N-dimethylacetamide , aceto...

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Abstract

The invention discloses a biaryl compound as well as a preparation method and application thereof. The preparation method comprises the following steps: reacting magnesium chips and lithium chloride in a schlenk sealed tube to obtain a reactant 1, adding ultra-dry tetrahydrofuran into the sealed tube, extracting nitrogen from the sealed tube, then adding aryl quaternary ammonium salt, a 5mol% catalyst, aryl bromide and N, N, N' N'-tetramethyldisiloxane, stirring and reacting at 25-60 DEG C for 6-12 hours to obtain a reactant 2, and finally, sequentially carrying out extracting, washing, drying, extract liquor removing and purifying on the reactant 2 to obtain the biaryl compound which can be used for preparing a compound containing a biaryl structure. The preparation method is wide in substrate range, convenient to operate, mild in reaction condition, low in pollution and high in economic benefit, and the obtained biaryl compound has good functional group tolerance and substrate universality.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, in particular to a biaryl compound and its preparation method and application. Background technique [0002] Biaryls are one of the most important parts of chemicals and have specific roles in the chemical and pharmaceutical industries. Recently, molecules containing biaryl-like structures have seen increasing applications in the fields of pharmaceuticals, agrochemicals, polymers, and materials. Therefore, it is necessary to develop more economical and efficient methods for the preparation of biaryl compounds. [0003] Quaternary ammonium salts are relatively simple to prepare by simply reacting a ubiquitous amine with an alkyl electrophile such as methyl iodide or methyl trifluoromethanesulfonate. In recent years, quaternary ammonium salts, as a multifunctional reagent, have been proved to be effective in participating in various organic transformation processes and realizing the pre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/00C07C17/263C07C25/18C07C41/30C07C43/225C07C67/343C07C69/76C07C69/94C07C209/68C07C211/48C07C213/00C07C217/80C07C253/30C07C255/46C07C319/20C07C321/28C07D213/30C07D307/79C07D307/91C07D317/22C07F7/18
CPCC07B37/00C07D317/22C07C41/30C07C209/68C07C319/20C07C253/30C07C67/343C07C17/2632C07F7/1892C07D307/79C07D307/91C07D213/30C07C213/00C07C43/225C07C211/48C07C321/28C07C255/46C07C69/76C07C25/18C07C217/80C07C69/94
Inventor 沈志良褚雪强张斯旋张晨
Owner NANJING UNIV OF TECH
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