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Method for synthesizing nitrobiphenyl compound

A synthesis method and technology of nitrobiphenyl, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of difficult industrialization, difficult acquisition of raw materials, low yield of products, etc., and achieve easy access, Avoidance of low temperature reactions, low technical and equipment requirements

Inactive Publication Date: 2013-10-23
TAIZHOU BAILLY CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0016] In order to overcome the existing defects in the prior art, such as the difficulty in obtaining raw materials, low product yield, low purity and difficulty in realizing industrialization, the present invention provides a new method for synthesizing nitrobiphenyl compounds , the method uses the readily available chemical products nitrobenzene and substituted halobenzenes as raw materials, and utilizes C-H activation means to realize the synthesis of the key intermediate 2-nitrobiphenyl of boscalid and its structural analogues , and the purification of the intermediate was achieved by using the purification method-recrystallization

Method used

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  • Method for synthesizing nitrobiphenyl compound
  • Method for synthesizing nitrobiphenyl compound
  • Method for synthesizing nitrobiphenyl compound

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Add 10mL of nitrobenzene and 1.92g of p-chlorobromobenzene, 0.11g of palladium acetate, 0.262g of triphenylphosphine and 4.88g of cesium carbonate into a 50mL three-necked flask equipped with a reflux condenser and a stirring device. Heated to 140°C for 24 hours. After the reaction, insoluble matter was filtered off, nitrobenzene was distilled off under reduced pressure, 5 mL of ethanol was added to the crude product, and refluxed for 0.5 hours. Then the insolubles were filtered off, and the filtrate was cooled and crystallized to obtain 1.65 grams of yellow crystal 4-chloro-2'-nitrobiphenyl, with a yield of 67% and a purity of 95%. Characterized by NMR as the target product: 1 H NMR (300MHz, CDCl 3 ): δ=7.24(d,J=6.0Hz,2H),7.38-7.42(m,3H),7.50-7.51(m,1H),7.62-7.63(m,1H),7.86-7.89(m,1H ) ppm.

Embodiment 2

[0041] Add 10 mL of nitrobenzene, 2.36 g of 1,4-dibromobenzene, 0.11 g of palladium acetate, 0.262 g of triphenylphosphine and 4.88 g of cesium carbonate into a 50 mL three-necked flask equipped with a reflux condenser and a stirring device, Under atmospheric conditions, it was heated to 140° C. to react for 24 hours. After the reaction, insoluble matter was filtered off, nitrobenzene was distilled off under reduced pressure, 5 mL of ethanol was added to the crude product, and refluxed for 0.5 hours. Then the insolubles were filtered off, and the filtrate was cooled and crystallized to obtain 1.93 grams of yellow crystal 4-bromo-2'-nitrobiphenyl, with a yield of 66% and a purity of 95%. Characterized by NMR as the target product: 1 H NMR (300MHz, CDCl 3 ): δ=7.23(d,J=6.0Hz,2H),7.37-7.40(m,3H),7.48-7.50(m,1H),7.61-7.63(m,1H),7.85-7.90(m,1H ) ppm.

Embodiment 3

[0043] Add 10 mL of nitrobenzene and 2.61 g of (4-bromophenyl) phenyl ketone, 0.11 g of palladium acetate, 0.262 g of triphenylphosphine and 4.88 g of carbonic acid in a 50 mL three-necked flask equipped with a reflux condenser and a stirring device cesium, heated to 140°C for 24 hours under nitrogen atmosphere. After the reaction, insoluble matter was filtered off, nitrobenzene was distilled off under reduced pressure, 5 mL of ethanol was added to the crude product, and refluxed for 0.5 hours. Then the insolubles were filtered off, and the filtrate was cooled and crystallized to obtain 2.25 grams of yellow crystal 4-benzoyl-2'-nitrobiphenyl, with a yield of 70% and a purity of 94%. Characterized by NMR as the target product:1 H NMR (300MHz, CDCl 3 ): δ=7.40-7.53(m,6H),7.55-7.59(m,1H),7.62-7.66(m,1H),7.84(t,J=8.4Hz,4H),7.89-7.95(m,1H ) ppm.

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Abstract

The invention relates to a method for synthesizing a nitrobiphenyl compound, and particularly relates to a method for synthesizing a nitrobiphenyl compound through C-H activation. The method is characterized in that chemical products, namely nitrobenzene and substituted halobenzene which are easy to obtain on the market, are used as raw materials, the synthesis of a key intermediate, namely 2-nitrobiphenyl of boscalid and analogues of the 2-nitrobiphenyl is realized by using a C-H activation means, and the purification of the intermediate is realized by using purification method-recrystallization. The method has atom economy and great potential and advantages in terms of industrialization. Compared with a conventional method, the method has the advantages that the two raw materials adopted by the method are easy to obtain and have the price advantages.

Description

technical field [0001] The invention relates to a method for synthesizing nitrobiphenyl compounds, in particular to a method for synthesizing nitrobiphenyl compounds through C-H activation. technical background [0002] Boscalid is a new type of nicotinamide fungicide developed by BASF in Germany. It is mainly used to prevent and control powdery mildew, gray mold, various rots, brown rots and root rots. The product was launched in 2004 Registered in UK, Germany and Switzerland. Boscalid belongs to the succinate coenzyme Q reductase inhibitor in the mitochondrial respiratory chain, which has a strong inhibitory ability to spore germination and has no cross-resistance with other fungicides. [0003] The important intermediate for the synthesis of boscalid is 2-aminobiphenyl (usually obtained by reducing the corresponding nitro compound in the prior art) as shown in the following formula (II), and the synthesis method of this intermediate has been patented WO9733846, CN102143...

Claims

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Application Information

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IPC IPC(8): C07C205/12C07C205/45C07C201/12
Inventor 姜冉刘志平焦德荣
Owner TAIZHOU BAILLY CHEM CO LTD
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