Preparation method of 5-chloro-2-methoxy cyanophenyl

A technology of methoxybenzonitrile and p-fluoronitrobenzene, which is applied in the field of preparation of 5-chloro-2-methoxybenzonitrile, can solve the unseen synthetic method of 5-chloro-2-methoxybenzonitrile Reporting and other issues, to achieve the effect of low price, high conversion rate of raw materials, and easy access

Inactive Publication Date: 2012-11-21
CHANGZHOU UNIV
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  • Abstract
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  • Application Information

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Problems solved by technology

[0003] At present, there is no relevant report on th

Method used

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Embodiment 1

[0021] (1) Bromination reaction: Add 7.095 g of p-fluoronitrobenzene and 12 g of acetic acid to the reaction vessel, and control the temperature of the water bath to 15 °C. 8.9 g of N-bromosuccinimide were added slowly with stirring. During the addition, the temperature should not exceed 15°C. After the addition, the reaction was incubated for 10 h, and the reaction ended. After the reaction was completed, the reactant was poured into 500 mL of ice water to precipitate a solid, which was filtered by suction and dried to obtain 10.23 g of 3-bromo-4-fluoronitrobenzene as a light yellow powder solid, with a yield of 93%.

[0022] (2) Nitro reduction reaction: Add 11.0 g of 3-bromo-4-fluoronitrobenzene to the reaction vessel, add water to 1 / 2 of the reaction vessel, add 2.5 g of ammonium chloride, raise the temperature to 70 °C, and batch Add 7.0 g of iron powder. During the addition, the temperature should not exceed 70 °C. After the addition, keep the temperature for 10 h to c...

Embodiment 2

[0027] (1) Bromination reaction: Add 7.095 g of p-fluoronitrobenzene and 20 g of acetic acid to the reaction vessel, and control the temperature of the water bath to 25 °C. 9.34 g of N-bromosuccinimide were added slowly with stirring. During the addition process, the temperature should not exceed 25°C. After the addition, the reaction was incubated for 4.5 h, and the reaction ended. After the reaction was completed, the reactant was poured into 500 mL of ice water to precipitate a solid, which was filtered by suction and dried to obtain 10.56 g of 3-bromo-4-fluoronitrobenzene as a light yellow powder solid, with a yield of 96.0%.

[0028] (2) Nitro reduction reaction: Add 11.0 g of 3-bromo-4-fluoronitrobenzene to the reaction vessel, add water to 1 / 2 of the reaction vessel, add 2.5 g of ammonium chloride, raise the temperature to 82 °C, and batch Add 9.8 g of iron powder. During the addition, the temperature should not exceed 85 °C. After the addition, keep the temperature f...

Embodiment 3

[0033] (1) Bromination reaction: Add 7.095 g of p-fluoronitrobenzene and 22 g of acetic acid into the reaction vessel, and control the temperature of the water bath to 35 °C. 9.34 g of N-bromosuccinimide were added slowly with stirring. During the addition process, the temperature should not exceed 35°C. After the addition, keep the temperature for 2.0 h to complete the reaction. After the reaction was completed, the reactant was poured into 500 mL of ice water to precipitate a solid, which was filtered by suction and dried to obtain 10.582 g of 3-bromo-4-fluoronitrobenzene as a light yellow powder solid, with a yield of 96.2%.

[0034] (2) Nitro reduction reaction: Add 11.0 g of 3-bromo-4-fluoronitrobenzene to the reaction vessel, add water to 1 / 2 of the reaction vessel, add 2.5 g of ammonium chloride, raise the temperature to 92 °C, and batch Add 9.8 g of iron powder. During the addition, the temperature should not exceed 95 °C. After the addition, keep the temperature for...

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Abstract

The invention discloses a preparation method of 5-chloro-2-methoxy cyanophenyl, relating to the technical field of medicine intermediates. The method is characterized by using fluoronitrobenzene as an initial raw material, and conducting bromination, nitro reduction, diazotization-Sandmeyer, Williamson substitution and carbonitriding to synthesize 5-chloro-2-methoxy cyanophenyl. The 5-chloro-2-methoxy cyanophenyl obtained by the method is a white powdery solid with the purity of 99.5%, the feed stock conversion each step respectively reaches 100%, and the total yield of the whole process reaches 48%.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical intermediates, in particular to a preparation method of 5-chloro-2-methoxybenzonitrile. Background technique [0002] At present, 5-chloro-2-methoxybenzonitrile is mainly used in medicine, pesticide and other industries. For example, it can be used for: 1) Synthesis of (Z)-ethyl-5-chloro-N-cyano-2-methoxybenzimidazole compounds for the treatment of diabetes and hypertension, etc. 2) Synthesis of compounds for the treatment of immune disorders and inflammatory diseases 3) Synthesis of ethyl-5-chloro-2-methoxybenzimidazole compound 4) Synthesis of 4,6-dichloro-2-(5-chloro-2-methoxyphenyl) pyrimidine compound for cancer treatment 7-Chloro-2-oxy-1,2,3,4-tetrahydroquinoxaline-5-carbonitrile used to protect neurons 5) Synthesis of arylpyrazoles and pyrroles with herbicidal and insecticidal properties Nitrile derivatives. [0003] At present, there is no relevant report on the synthesis method ...

Claims

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Application Information

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IPC IPC(8): C07C255/54C07C253/14
Inventor 陈兴权王林董燕敏郝永兵蒋锐殷杰
Owner CHANGZHOU UNIV
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