A kind of method utilizing bromoarylsulfonyl fluoride to prepare unsymmetrical terphenyl compound

A sulfonyl fluoride, asymmetric technology, applied in the field of preparing asymmetric terphenyl compounds, can solve the problems of complicated operation, low product yield, harsh reaction conditions, etc., to simplify the operation process, simplify the reaction operation steps, increase the Effects of synthetic pathways

Active Publication Date: 2020-01-07
ZUNYI MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention intends to provide a method for preparing asymmetric terphenyl compounds by using bromoarylsulfonyl fluoride, which solves the problems of low product yield, complicated operation and harsh reaction conditions in traditional synthesis methods

Method used

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  • A kind of method utilizing bromoarylsulfonyl fluoride to prepare unsymmetrical terphenyl compound
  • A kind of method utilizing bromoarylsulfonyl fluoride to prepare unsymmetrical terphenyl compound
  • A kind of method utilizing bromoarylsulfonyl fluoride to prepare unsymmetrical terphenyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the preparation of 4-aminoterphenyl

[0020]

[0021] In air, add 1mmol 4-bromoarylsulfonyl fluoride, 1mmol 4-aminophenylboronic acid, 1mmol potassium phenyltrifluoroborate, 0.01mmol palladium acetate, 2mmol potassium carbonate, 4mL ethanol, 4mL water into a round bottom flask In the reaction, stir at 25°C for 1 hour, then add 2mmol triethylamine, 0.01mmol palladium acetate to the reaction, and increase the temperature to 80°C, react for 2 hours, after the reaction, add ethyl acetate to quench the reaction, the reaction The mixture was concentrated by a rotary evaporator and separated by column chromatography to obtain an analytically pure asymmetric terphenyl compound with a yield of 88%. The structure of the product was confirmed by H NMR and C NMR analysis. 1H NMR (400MHz, CDCl 3 )δ7.63(d, J=7.6Hz, 6H), 7.51–7.38(m, 5H), 7.34(t, J=7.3Hz, 1H), 6.77(d, J=8.3Hz, 2H), 4.05( s,2H). 13 C NMR (101MHz, CDCl 3 )δ152.0, 145.2, 144.8, 143.0, 133.6, 132.2, 1...

Embodiment 2

[0022] Embodiment 2: the preparation of 4-cyano p-terphenyl

[0023]

[0024] In air, add 1mmol 4-bromoarylsulfonyl fluoride, 1mmol 4-cyanophenylboronic acid, 1mmol potassium phenyltrifluoroborate, 0.01mmol palladium acetate, 2mmol potassium carbonate, 4mL ethanol, 4mL water into the round bottom In the flask, the reaction was carried out with stirring at 25° C. for 1 hour, then 3 mmol triethylamine and 0.01 mmol palladium acetate were added to the reaction, and the temperature was increased to 80° C., and the reaction was carried out for 2 hours. After the reaction was completed, ethyl acetate was added to quench the reaction. The reaction mixture was concentrated with a rotary evaporator and separated by column chromatography to obtain an analytically pure asymmetric terphenyl compound with a yield of 92%. The structure of the product was confirmed by H NMR and C NMR analysis. 1H NMR (400MHz, CDCl 3 )δ7.79–7.60(m,10H),7.48(t,J=7.5Hz,2H),7.39(t,J=7.4Hz,1H). 13 C NMR (101...

Embodiment 3

[0025] Embodiment 3: the preparation of 4-formyl p-terphenyl

[0026]

[0027] In air, add 1mmol 4-bromoarylsulfonyl fluoride, 1mmol 4-formylphenylboronic acid, 1mmol potassium phenyl trifluoroborate, 0.01mmol palladium acetate, 4mmol potassium carbonate, 4mL ethanol, 4mL water into the round bottom In the flask, the reaction was carried out with stirring at 25° C. for 1 hour, then 2 mmol triethylamine and 0.01 mmol palladium acetate were added to the reaction, and the temperature was increased to 80° C., and the reaction was carried out for 2 hours. After the reaction was completed, ethyl acetate was added to quench the reaction. The reaction mixture was concentrated by a rotary evaporator and separated by column chromatography to obtain an analytically pure asymmetric terphenyl compound with a yield of 81%. The structure of the product was confirmed by H NMR and C NMR analysis. 1H NMR (400MHz, CDCl 3 )δ10.07(s,1H),7.98(d,J=8.1Hz,2H),7.81(d,J=8.1Hz,2H),7.73(s,4H),7.69–7.6...

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Abstract

The invention discloses a method for preparing asymmetric terphenyl compound by using brominated aryl sulfuryl fluoride, which belongs to the technical field of organic synthetic chemistry. The methodcomprises the following steps: adding brominated aryl sulfuryl fluoride, arylboronic acid, aryl potassium trifluoroborate, a palladium catalyst, inorganic base, ethanol and water in a flask in order,stirring the materials at the temperature of 20-40 DEG C, reacting the materials for 0.5-2 h and adding organic base in the flask, and heating the materials to the temperature of 80-100 DEG C for a continuous reaction for 2-6 h; after a reaction is completed, adding ethyl acetate in the flask, uniformly stirring the materials, transferring a mixture in the flask to a rotary evaporation instrumentfor steaming a solvent, and performing column chromatography separating on a concentrate to obtain the analytically pure asymmetric terphenyl compound. During a whole synthetic method process, an intermediate product is required for being separated, the reaction operation steps can be simplified, ethanol and water are taken as the solvent in the reaction, the environment pollution problem due tothe toxic organic solvent can be solved, the reaction yield is high, and a synthesis approach of the asymmetric terphenyl compound is increased.

Description

technical field [0001] The invention relates to the technical field of organic synthesis chemistry, in particular to a method for preparing unsymmetrical terphenyl compounds by using bromoarylsulfonyl fluoride. Background technique [0002] Terphenyl compounds are a class of compounds composed of three benzene rings linked by carbon-carbon bonds. It has been reported in the literature that these compounds have a variety of biological activities, including immunosuppression, anti-oxidation, neuroprotection and antithrombotic, etc., and the terphenyl structure is also an important structural unit of many liquid crystal material molecules, so terphenyl compounds are used in medicine and The field of materials has important application potential. According to the similarities and differences of the functional groups carried by the benzene rings on both sides, terphenyl compounds are divided into symmetrical terphenyls and asymmetric terphenyls. At present, a large number of li...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/68C07C211/45C07C253/30C07C255/50C07C45/68C07C47/546C07C41/30C07C43/205C07C49/84C07C47/575C07C43/225
CPCC07C41/30C07C45/68C07C209/68C07C253/30C07C211/45C07C255/50C07C47/546C07C43/205C07C49/84C07C47/575C07C43/225C07C43/2055
Inventor 李新民袁泽利滕勇
Owner ZUNYI MEDICAL UNIVERSITY
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