Method for preparing 2-iodine-5-phenylpyridine

A technology of phenylpyridine and iodonium salt, applied in the industrial production field of 2-iodo-5-phenylpyridine, can solve problems such as high cost and unsuitability for production, and achieve the effects of improving income, saving production cost and stabilizing process conditions

Active Publication Date: 2014-05-28
BENGBU CHINA SYNCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method literature molar yield only has 45%, and uses a large a...

Method used

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  • Method for preparing 2-iodine-5-phenylpyridine

Examples

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Embodiment 1

[0023] A 10-liter glass reactor is equipped with mechanical stirring and a thermometer. Under the protection of nitrogen, add 500 g of raw material 2-chloro-5-phenylpyridine, a certain amount of cuprous iodide and 1,10-phenanthroline, relative to the raw material 2-chloro -5-Phenylpyridine 1.1 molar equivalents of sodium iodide, 3 liters of dimethyl sulfoxide as a solvent, heated to 160 ° C for reaction, stop the reaction when there is no raw material 2-chloro-5-phenylpyridine remaining in the system, drop To room temperature, distill under reduced pressure to recover the solvent dimethyl sulfoxide, so that it can be used mechanically next time, add 2 liters of tetrahydrofuran to the residue in the reactor, stir for half an hour, filter with suction, and concentrate the filtrate to dryness to obtain the product 2-iodo-5- For the crude product of phenylpyridine, a certain amount of methanol was added to the crude product for recrystallization to obtain the pure product with a mo...

Embodiment 2

[0025] A 10-liter glass reactor is equipped with a mechanical stirrer and a thermometer. Under the protection of nitrogen, add 500 g of the raw material 2-chloro-5-phenylpyridine, a certain amount of cuprous iodide and 1,2-cyclohexanediamine, relative to the raw material 2- Chloro-5-phenylpyridine 1.1 molar equivalent of potassium iodide, 3 liters of N,N-dimethylformamide as a solvent, heated to 150°C to react, stop when there is no raw material 2-chloro-5-phenylpyridine remaining in the system Reaction, lowered to room temperature, and the solvent N,N-dimethylformamide was recovered by distillation under reduced pressure, so as to be used mechanically next time, 2 liters of ethyl acetate was added to the residue in the reactor, stirred for half an hour, filtered with suction, and the filtrate was concentrated to dryness , to obtain the crude product of 2-iodo-5-phenylpyridine, a certain amount of ethanol was added to the crude product, and recrystallized to obtain the pure pro...

Embodiment 3

[0027] A 10-liter glass reactor is equipped with a mechanical stirrer and a thermometer. Under the protection of nitrogen, add 500 g of raw materials 2-chloro-5-phenylpyridine, a certain amount of cuprous iodide and N,N'-dimethyl-1,2-cyclo Hexamethylenediamine, 1.1 molar equivalents of potassium iodide relative to the raw material 2-chloro-5-phenylpyridine, 3 liters of N-methylpyrrolidone as a solvent, heated to 150°C for reaction, when there is no raw material 2-chloro-5-benzene in the system Stop the reaction when base pyridine remains, drop to room temperature, and recover the solvent N-methylpyrrolidone by distillation under reduced pressure, so that it can be used mechanically next time, add 2 liters of 1,2-dichloroethane to the residue in the reactor, stir for half an hour, After suction filtration, the filtrate was concentrated to dryness to obtain the crude product 2-iodo-5-phenylpyridine. A certain amount of ethanol was added to the crude product for recrystallization ...

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Abstract

The invention provides a method for preparing 2-iodine-5-phenylpyridine and relates to the field of an industrial production technology of 2-iodine-5-phenylpyridine. The method comprises the following steps: selecting 2-chlorine-5-phenylpyridine as an initial raw material, carrying out a halogen replacement reaction between 2-chlorine-5-phenylpyridine and inorganic iodine salt in the presence of a catalyst and a ligand, and simply processing to obtain 2-iodine-5-phenylpyridine with high purity and high yield. The method provided by the invention requires no high-temperature and high-pressure reaction, has a safe and stable technology and is suitable for large-scale production. The raw materials used are noncorrosive to production equipment, and solvents used all can be recovered and reused. Thus, the method accords with the concept of green chemistry. The harm of environmental pollution is reduced, and production cost is saved. Purity and yield of the product are both high, thus effectively raising benefits of a manufacturing enterprise.

Description

technical field [0001] The invention relates to the technical field of industrial production of 2-iodo-5-phenylpyridine, in particular to a method for preparing 2-iodo-5-phenylpyridine. Background technique [0002] 2-iodo-5-phenylpyridine is an important raw material for the preparation of marine alkaloid Clathryimine B, which is a newly discovered extract of Indian Ocean coral Clathrya basilana [Tetrahedron Letters, Vol.37, 1996, p2389-2390], Its structure is very novel, different from general polypeptides and terpenoids, and the research on the biological activity of Clathryimine B has just begun worldwide. Therefore, the development of a simple, efficient, and environmentally friendly synthesis process for 2-iodo-5-phenylpyridine has very important forward-looking significance for the study of clathryimine B. [0003] At present, the methods for preparing 2-iodo-5-phenylpyridine mainly contain the following: [0004] 1. U.S. Patent No. 4,971,982 (1990) uses 2-chloro-5-...

Claims

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Application Information

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IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 杨青张浩赵士民徐剑霄刘兴华
Owner BENGBU CHINA SYNCHEM TECH CO LTD
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