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A kind of synthetic method of 3-chloro-4-(3-fluorobenzyloxy) nitrobenzene

A technique for the synthesis of fluorobenzyloxy, which is applied in the field of synthesis of 3-chloro-4-nitrobenzene, can solve problems such as low yield, high irritation of m-fluorobenzyl bromide, and great harm to human body, and achieve the product High yield, easy industrial production, and high purity

Active Publication Date: 2019-04-09
SHANDONG BOYUAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This reaction usually has a low yield, and the m-fluorobenzyl bromide used in the synthesis process is more irritating. If it is used for a long time, it will be harmful to the human body and is not conducive to industrial production.

Method used

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  • A kind of synthetic method of 3-chloro-4-(3-fluorobenzyloxy) nitrobenzene
  • A kind of synthetic method of 3-chloro-4-(3-fluorobenzyloxy) nitrobenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 350ml tetrahydrofuran, 75g 2-chloro-4-nitrophenol, 57.2g 3-fluorobenzyl alcohol and 104.9g tributylphosphine into a 1000ml reaction flask, start stirring, cool down to 10°C, and slowly add 89.3g tetramethyl A mixed solution composed of azodicarbonamide (TMAD) and 200ml tetrahydrofuran, after the dropwise addition is completed, the temperature is controlled at 10°C and the reaction is stirred for 2 hours. 200ml of dimethylformamide was stirred and dissolved, cooled to 0°C for recrystallization, suction filtered, and the obtained solid was dried at 55-60°C to obtain 112.7g of light yellow solid with a purity of 99.89% and a yield of 92.6%.

Embodiment 2

[0020] Add 350ml tetrahydrofuran, 75g 2-chloro-4-nitrophenol, 58.0g 3-fluorobenzyl alcohol and 106g tributylphosphine into a 1000ml reaction flask, start stirring, cool down to 10°C, and slowly add 90g tetramethylazo A mixed solution composed of dimethylamide (TMAD) and 200ml tetrahydrofuran, the dropwise addition is completed, the temperature is controlled at 10°C and the reaction is stirred for 1.5 hours. 200ml of methylformamide was stirred and dissolved, cooled to 0°C for recrystallization, filtered with suction, and the resulting solid was dried at 55-60°C to obtain 113.2g of a light yellow solid with a purity of 99.82% and a yield of 93.0%.

Embodiment 3

[0022] Add 350ml tetrahydrofuran, 75g 2-chloro-4-nitrophenol, 57.2g 3-fluorobenzyl alcohol and 100.0g tributylphosphine to a 1000ml reaction flask, start stirring, cool down to 10°C, and slowly add 85.0g tetramethyl A mixed solution composed of azodicarbonamide (TMAD) and 180ml tetrahydrofuran, the dropwise addition is completed, the temperature is controlled at 10°C and the reaction is stirred for 3 hours. - 200ml of dimethylformamide was stirred and dissolved, cooled to 0°C for recrystallization, filtered with suction, and the obtained solid was dried at 55-60°C to obtain 112.5g of a light yellow solid with a purity of 99.93% and a yield of 92.5%.

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PUM

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Abstract

The invention discloses a synthesis method of 3-chloro-4-(3-fluorobenzoyl)nitrobenzene. According to the method, tributyl phosphine and tetramethylazodicarbonamide are used as catalysts, and 2-chloro-4-nitrophenol and 3-fluorobenzyl alcohol react to generate the 3-chloro-4-(3-fluorobenzoyl)nitrobenzene. According to the method disclosed by the invention, the synthesis yield is improved, and the utilization of m-fluorobenzyl bromide is avoided, so that the synthesis method is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of 3-chloro-4-(3-fluorobenzyloxy)nitrobenzene, which belongs to the technical field of medicine synthesis. Background technique [0002] Lapatinib, an anticancer drug developed by GlaxoSmithKline, has a chemical name of N-(3-chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5- (((2-(methylsulfonyl)ethyl)amino)methyl)-2-furyl)-4-quinazolinamine di-p-toluenesulfonate monohydrate. Approved by the FDA in March 2007, it is used in combination with capecitabine for the treatment of advanced human epidermal growth factor receptor 2 overexpression and previous treatment including anthracyclines, taxanes and trastuzumab or metastatic breast cancer. In combination with letrozole for the treatment of postmenopausal women with hormone receptor-positive metastatic breast cancer overexpressing the HER2 receptor. In recent years, there have been more and more studies on lapatinib in other tumor treatment fields. [0003] 3-C...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/12C07C205/37
CPCC07C201/12C07C205/37
Inventor 赵孝杰张敏刘远慧
Owner SHANDONG BOYUAN PHARM CO LTD
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