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Preparation method of 2-fluoro-5-bromoxynil

A technology of bromoxynil and o-fluorobromobenzene is applied in the field of preparation of pharmaceutical intermediate 2-fluoro-5-bromobenzonitrile, and achieves the effects of reduced pollution and toxicity, mild reaction conditions and cheap raw materials

Active Publication Date: 2010-12-01
溧阳常大技术转移中心有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on its related synthetic method at present, so it is necessary to develop a synthetic route

Method used

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  • Preparation method of 2-fluoro-5-bromoxynil

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] ① Add 70g 40% HBr, 70ml HBr to a 250ml flask 2 O, 11.1g o-fluoroaniline, heated to 70-80°C for reaction. Cool down to 40-50°C, add 7.2g CuBr, and stir well. Add 8.3g NaNO dropwise 2 , 25ml H 2 O is made into the solution, after dripping, keep warm and react until the end. Cool down to room temperature, pour 200ml H 2 In O, the organic layer was separated, and the organic layer was washed with water to be close to neutral, and anhydrous Na 2 SO 4 Dry, filter with suction, and then distill under reduced pressure to obtain 14.4 g of o-fluorobromobenzene as a light yellow transparent liquid with a yield of 82.8%.

[0014] ②Add 40ml of DMF, 11.7g of CuCN, and 17.4g of o-fluorobromobenzene into a 250ml flask, heat to 150°C, and react for 5h. After the reaction, steam distillation was carried out to obtain 7.26 g of o-fluorobenzonitrile as a yellow transparent liquid with a yield of 60%.

[0015] ③ Add 20ml of concentrated H to a 100ml flask 2 SO 4 , 6.05g o-fluorobe...

Embodiment 2

[0017] ① Add 70g 40% HBr, 70ml HBr to a 250ml flask 2 O, 11.1g o-fluoroaniline, heated to 70-80°C for reaction. Cool down to 40-50°C, add 7.2g CuBr, and stir well. Add 6.9g NaNO dropwise 2 , 21ml H 2 O is made into the solution, after dripping, keep warm and react until the end. Cool down to room temperature, pour 200ml H 2 In O, the organic layer was separated, and the organic layer was washed with water to be close to neutral, and anhydrous Na 2 SO 4 Dry, filter with suction, and then distill under reduced pressure to obtain 10.4 g of o-fluorobromobenzene as a light yellow transparent liquid with a yield of 60%.

[0018] ②Add 40ml of DMF, 11.7g of CuCN, and 17.4g of o-fluorobromobenzene into a 250ml flask, heat to 150°C, and react for 5h. After the reaction, steam distillation was carried out to obtain 7.26 g of o-fluorobenzonitrile as a yellow transparent liquid with a yield of 60%.

[0019] ③ Add 20ml of concentrated H to a 100ml flask 2 SO 4 , 6.05g o-fluorobenz...

Embodiment 3

[0021] ① Add 70g 40% HBr, 70ml HBr to a 250ml flask 2 O, 11.1g o-fluoroaniline, heated to 70-80°C for reaction. Cool down to 40-50°C, add 7.2g CuBr, and stir well. Add 7.6g NaNO dropwise 2 , 23ml H 2 O is made into the solution, after dripping, keep warm and react until the end. Cool down to room temperature, pour 200ml H 2 In O, the organic layer was separated, and the organic layer was washed with water to be close to neutral, and anhydrous Na 2 SO 4 Dry, filter with suction, and then distill under reduced pressure to obtain 12.4 g of o-fluorobromobenzene as a light yellow transparent liquid with a yield of 71%.

[0022]②Add 40ml of DMF, 11.7g of CuCN, and 17.4g of o-fluorobromobenzene into a 250ml flask, heat to 150°C, and react for 5h. After the reaction, steam distillation was carried out to obtain 7.26 g of o-fluorobenzonitrile as a yellow transparent liquid with a yield of 60%.

[0023] ③ Add 20ml of concentrated H to a 100ml flask 2 SO 4 , 6.05g o-fluorobenzo...

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Abstract

The invention relates to a preparation method of 2-fluoro-5-bromoxynil. The 2-fluoro-5-bromoxynil as a medicine intermediate is obtained by using 4-bromo-2-fluorobiphenyl as a raw material through three-step finishing synthesis of brominating diazonium, cyaniding and brominating, and the total yield of the method reaches 39.7 percent. In the cyaniding process, cuprous cyanide with lower toxicity is adopted to replace virulent sodium cyanide or potassuim cyanide; and in the brominating process, environment-friendly NBS and dibromohydantoin are adopted as brominating agents. The pollution and the toxicity of the whole process are greatly reduced. The preparation method has the advantages of cheap raw materials and mild reaction condition, thereby being an optimal process for synthesizing the 2-fluoro-5-bromoxynil.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate 2-fluoro-5-bromoxynil. Background technique [0002] 2-Fluoro-5-bromoxynil is widely used as an important pharmaceutical intermediate, for example, it can be synthesized 1) a novel cinnamic amide compound (2-isopropylphenyl)[2 -cyano-4-(E-((4-morpholine)carbonyl)ethyl)phenyl]sulfide (Link James, Liu Gang, Pei Zhonghua.Preparation of 2-or 4-(phenylthio)cinnamidesas cell adhesion- inhibiting antiinflammatory and immune-suppressive compounds.US, 6878700[P].2005-04-12); 2) thieno[3,2-d]-pyrimidin-4-one compounds for cancer chemotherapy, such compounds Can inhibit the activity of Pim kinases (Wang Le, Hasvold Lisa A., Tao Zhi-Fu.Preparation of thieno[3,2-d]pyrimidin-4-ones for use as cancer chemotherapy which inhibit the activity ofPim kinases.US, 2009030196[ P].2009-01-29); 3) indazole compounds, which can be used as glucokinase activators for treating diabetes and obesity (Ya...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/50C07C253/30
Inventor 陈兴权赵万胜董燕敏卿鹏程
Owner 溧阳常大技术转移中心有限公司
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