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A kind of synthetic method of 2,5-dibromoiodobenzene

A technology of dibromoiodobenzene and a synthesis method is applied in the synthesis of 2,5-dibromoiodobenzene and the field of preparation of halobenzene compounds, and can solve the problems of difficult control of mono-substituted products, low yield and high production cost, Achieve the effect of improving iodination reaction activity, easy industrial production, and avoiding ultra-low temperature reaction

Active Publication Date: 2018-04-20
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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  • A kind of synthetic method of 2,5-dibromoiodobenzene

Examples

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Effect test

example 1

[0012] In a dry 500 mL three-necked flask, add 1,4-dibromobenzene (47.2 g, 0.2 mol) and iron trifluoroacetate (79 g, 0.2 mol), and dissolve iodine (50.8 g, 0.2 mol) in 200 mL of chloroform was slowly added dropwise to the reaction system under reflux conditions, the reaction temperature was controlled at 65 ℃, and the reaction was stirred for 8 hours. After the reaction was stirred for 8 hours, the reaction was completed by GC. Wash with 200 mL of saturated sodium sulfite aqueous solution, wash with 500 mL of water, separate into layers, and combine the organic layers. The solvent was recovered under reduced pressure to obtain an off-white solid, which was recrystallized with 120 mL of isopropanol to obtain 54.6 g of 2,5-dibromoiodobenzene as a white solid product with a purity greater than 99% (GC) and a yield of 75.4%.

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

[0014] 1 H NMR (400 MHz, DMSO-d 6 ): 8.127-8.121 (d, 1H; J=2.4Hz), 7.664-7.642 (d, 1H; J=8.8Hz...

example 2

[0017] In a dry 2 L three-neck flask, add 1,4-dibromobenzene (118 g, 0.5 mol) and iron trifluoroacetate (197.5 g, 0.5 mol), and dissolve the iodine element (101.6 g, 0.4 mol) in 500 In mL chloroform, slowly drip into the reaction system under reflux conditions, control the reaction temperature to 75 ℃, stir the reaction for 10 hours, GC detects that the reaction is complete, wash with 500 mL saturated sodium sulfite aqueous solution, wash with 2 L water, separate the layers, combine the organic layers, reduce The solvent was recovered by pressure to obtain an off-white solid, which was recrystallized with 250 mL of isopropanol to obtain 139.8 g of 2,5-dibromoiodobenzene as a white solid product with a purity greater than 99% (GC) and a yield of 77.3%.

example 3

[0019] In a dry 1 L three-necked flask, add 1,4-dibromobenzene (70.8 g, 0.3 mol) and iron trifluoroacetate (142.2 g, 0.36 mol), and dissolve the elemental iodine (91.4 g, 0.36 mol) in 300 In mL of chloroform, slowly drip into the reaction system under reflux conditions, control the reaction temperature to 70 ℃, stir the reaction for 10 hours, GC detects that the reaction is complete, wash with 500 mL of saturated sodium sulfite aqueous solution, wash with 1 L of water, separate into layers, combine the organic layers, reduce The solvent was recovered by pressure to obtain an off-white solid, which was recrystallized with 150 mL of isopropanol to obtain 82.6 g of 2,5-dibromoiodobenzene as a white solid product 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, belonging to the field of organic synthesis. Background technique [0002] 2,5-Dibromoiodobenzene is a very important raw material for fine chemicals. It is a halide of 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 methods of 2,5-dibromoiodobenzene reported in the domestic and foreign literature mainly use 1,4-dibromobenzene as the starting material, in tetrahydrofuran and other organic solvents, the temperature is below -80℃ 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). The synthesis method needs to be carried out at an ultra-low temperature of -80°C, and the operation...

Claims

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Application Information

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Patent Type & Authority Patents(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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