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A kind of method of green synthesis 2,5-dibromo-1,4-diiodobenzene intermediate

A technology of green synthesis and diiodobenzene, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, preparation of halogenated hydrocarbons, etc., can solve human and environmental disasters, difficult to remove elemental iodine, Difficulty in product purification and other problems, to achieve the effect of increasing yield, reducing operational risk, and optimizing reaction scheme

Active Publication Date: 2022-05-27
大连金点生物科技有限公司
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Problems solved by technology

[0003] However, there are some problems in the traditional process method. Concentrated sulfuric acid and elemental iodine are used in the iodination reaction. The elemental iodine in the product is difficult to remove, and the final product is difficult to purify. The purity cannot meet the standards for the application of organic photoelectric materials, and the reaction time is long. , high temperature, poor selectivity, poor yield, and finally also produce pollutants such as inorganic acid and organic iodine; the increase in cost has brought inevitable disasters to people and the environment.

Method used

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  • A kind of method of green synthesis 2,5-dibromo-1,4-diiodobenzene intermediate
  • A kind of method of green synthesis 2,5-dibromo-1,4-diiodobenzene intermediate
  • A kind of method of green synthesis 2,5-dibromo-1,4-diiodobenzene intermediate

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Experimental program
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Effect test

Embodiment 1

[0012] Example 1: 3-Bromo-4-methylpyridine

[0013]

[0014] 1,4-Dibromobenzene (10 g, 0.043 moL), I-OMe (11 g, 0.0473 moL), DTBPF (1.0 g, 0.0021 moL), TfOH (2 mL, 0.021 mol) were added to the three-necked flask in turn. moL), 1,2-dichloroethane DCE (120 mL). Stir at room temperature for 5 h, and after the reaction is completed, add 30 mL of saturated sodium bicarbonate solution to quench the reaction. After multiple extractions with dichloromethane, the organic phases were combined, dried, and spin-dried to obtain a crude product, which was recrystallized from anhydrous ethanol to obtain the final product 2,5-dibromo-1,4-diiodobenzene. Yield 80%. MS (EI): m / z: 487.70 ([M] + )

Embodiment 2

[0015] Embodiment 2: this new process and traditional process productivity and cost comparison table

[0016] Table 1 Yield balance table of new process and traditional process

[0017]

[0018] As can be seen from above table 1, the purity 95% yield of 2,5-dibromo-1,4-diiodobenzene in the traditional technique is 60%, and in the new technique, 2,5-dibromo-1,4-diiodobenzene The purity of 99.9%, the total yield of 80%, increased from the original 12.6g to 16.8g. Not only does it reduce costs, but it also increases productivity, increases plant revenue, and improves profits. The most important thing is that the purity of the final product is very high, which meets the application requirements of organic optoelectronic materials. The improved process, safety and environmental protection have been significantly improved, the post-processing is relatively easy, and the process is green and environmentally friendly.

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Abstract

A green method for synthesizing 2,5-dibromo-1,4-diiodobenzene intermediate belongs to the technical field of organic photoelectric material intermediates. The method adopts organic ring hypervalent iodine as an iodination reagent, metal organophosphorus as a catalyst, trifluoromethanesulfonic acid as an additive, and 1,2-dichloroethane as a solvent. The ortho iodination of dibromobenzene was experimented with the activation of the ortho C‑H bond by the weak positioning group bromine. After the reaction, the solvent is removed to directly obtain 2,5-dibromo-1,4-diiodobenzene. The method solves the problems of poor purity and poor selectivity of the iodination reaction in the traditional method, and realizes a high-purity, high-efficiency, and high-selectivity iodination reaction of p-dibromobenzene. Adopting this optimized synthetic route has many advantages such as greatly increased yield, reduced cost, enhanced safety, energy saving, etc., and meets the modern chemical production requirements of green reaction.

Description

technical field [0001] A method for green synthesis of 2,5-dibromo-1,4-diiodobenzene intermediates belongs to the technical field of organic photoelectric material intermediates. Background technique [0002] 2,5-Dibromo-1,4-diiodobenzene is used as an intermediate of organic optoelectronic materials, mainly used in the synthesis of OLED light-emitting materials, host materials, electron transport materials and hole transport materials, etc. 2,5-dibromo- As the most important intermediate in organic optoelectronic materials, 1,4-diiodobenzene is of great significance. [0003] However, there are some problems in the traditional process. Concentrated sulfuric acid and elemental iodine are used in the iodination reaction. The elemental iodine in the product is difficult to remove, the final product is difficult to purify, the purity does not meet the application standard of organic optoelectronic materials, and the reaction time is long , the temperature is high, the selectiv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C17/12C07C25/02B01J31/22B01J31/02
CPCC07C17/12B01J31/2295B01J31/0267B01J2231/4277B01J2531/0225B01J2531/842C07C25/02
Inventor 金凤
Owner 大连金点生物科技有限公司
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