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Synthesis method for 2,5-dibromo-iodobenzene

A technique for the synthesis of dibromoiodobenzene and its synthesis method, which is applied in the field of preparation of halobenzene compounds and the synthesis of 2,5-dibromoiodobenzene, and can solve problems such as difficult control of monosubstituted products, high production cost, and low yield , to improve iodination reaction activity, avoid ultra-low temperature reaction, and facilitate industrial production

Active Publication Date: 2016-07-13
郑州金上化成新材料有限公司
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Problems solved by technology

This synthesis method needs to be carried out at -80°C ultra-low temperature, the operation is dangerous and complicated, the production cost is high, and it is difficult for industrial production
In addition, using 1,4-dibromobenzene as the starting material, 2,5-dibromoiodobenzene was synthesized by the conventional iodination method. The main problem is that the monosubstituted product obtained by the iodination reaction is difficult to control, and the product is mainly diiodine product. Mainly, difficult to separate, low yield, high production cost, not suitable for quantitative production

Method used

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  • Synthesis method for 2,5-dibromo-iodobenzene

Examples

Experimental program
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Effect test

example 1

[0012] In a dry 500mL three-neck flask, add 1,4-dibromobenzene (47.2g, 0.2mol) and iron trifluoroacetate (79g, 0.2mol), and dissolve iodine (50.8g, 0.2mol) in 200mL chloroform , slowly added dropwise to the reaction system under reflux conditions, controlled the reaction temperature at 65°C, stirred and reacted for 8 hours, GC detected that the reaction was complete, washed with 200mL saturated aqueous sodium sulfite solution, washed with 500mL water, separated into layers, combined the organic layers, and recovered the solvent under reduced pressure to obtain An off-white solid was recrystallized with 120 mL of isopropanol to obtain 54.6 g of a white solid product, 2,5-dibromoiodobenzene, with a purity greater than 99% (GC), and a yield of 75.4%.

[0013] Product melting point: 38.1-39.6°C, Ms(m / z): 361(M + ).

[0014] 1 HNMR (400MHz, DMSO-d 6 ): 8.127-8.121 (d, 1H; J=2.4Hz), 7.664-7.642 (d, 1H; J=8.8Hz), 7.531-7.504 (dd, 1H; J 1 =8.5Hz;J 2 =2.3Hz).

[0015] 13 CNMR (4...

example 2

[0017] In a dry 2L three-neck flask, add 1,4-dibromobenzene (118g, 0.5mol) and iron trifluoroacetate (197.5g, 0.5mol), and dissolve iodine (94.3g, 0.4mol) in 500mL of chloroform , slowly added dropwise to the reaction system under reflux conditions, the reaction temperature was controlled at 75°C, and after stirring for 10 hours, the reaction was detected by GC. It was washed with 500 mL of saturated aqueous sodium sulfite solution, washed with 2 L of water, separated into layers, combined with the organic layer, and the solvent was recovered under reduced pressure to obtain a The white solid was recrystallized with 250 mL of isopropanol to obtain 139.8 g of the white solid product 2,5-dibromoiodobenzene, with a purity greater than 99% (GC), and a yield of 77.3%.

example 3

[0019] In a dry 1L three-neck flask, add 1,4-dibromobenzene (70.8g, 0.3mol) and iron trifluoroacetate (142.2g, 0.36mol), and dissolve iodine (91.4g, 0.36mol) in 300mL of chloroform , slowly added dropwise to the reaction system under reflux conditions, controlled the reaction temperature at 70°C, stirred and reacted for 10 hours, GC detected that the reaction was complete, washed with 500mL of saturated aqueous sodium sulfite solution, washed with 1L of water, separated into layers, combined the organic layers, and recovered the solvent under reduced pressure to obtain The off-white solid was recrystallized with 150 mL of isopropanol to obtain 82.6 g of a white solid product, 2,5-dibromoiodobenzene, with a purity greater than 99% (GC), and a yield of 76.1%.

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Abstract

The invention discloses a novel synthesis method for 2,5-dibromo-iodobenzene and belongs to the field of organic chemistry synthesis.The synthesis method includes the steps that with 1,4-dibromo-benzene being a starting raw material, trifluoroacetic acid and iodine are subjected to an iodination reaction to synthesize the target product 2,5-dibromo-iodobenzene.The method avoids low-temperature reaction, is easy to implement, generates a small number of by-products, is suitable for industrialized production and has good application prospects.2,5- dibromo-iodobenzene is an important fine chemical intermediate and is widely applied to the fields of synthesis medicine, pesticide, dye, plastics, functional polymer materials and others.

Description

technical field [0001] The invention relates to a preparation method of halobenzene compounds, in particular to a synthesis method of 2,5-dibromoiodobenzene, which belongs to the field of organic synthesis. Background technique [0002] 2,5-Dibromoiodobenzene is a very important raw material for fine chemicals. It is a halogenated benzene and is a white solid. It is mainly used in the synthesis of medicines, pesticides, dyes, plastics and functional polymer materials. At present, the preparation method of 2,5-dibromoiodobenzene reported in the literature at home and abroad is mainly based on 1,4-dibromobenzene as the starting material, in organic solvents such as tetrahydrofuran, through tetramethylpiperidinyl Lithium reacts, and then continues to react with iodine to obtain 2,5-dibromoiodobenzene (European Journal of Organic Chemistry, (10), 1797-1801; 2008). This synthesis method needs to be carried out at -80°C ultra-low temperature, the operation is dangerous and comple...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/02C07C17/12
CPCC07C17/12C07C25/02
Inventor 屈凤波杨瑞娜杨振强陈辉孙敏青
Owner 郑州金上化成新材料有限公司
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