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Industrial production method of 1, 4-dibromo-2, 5-diiodobenzene

A production method and technology of diiodobenzene, applied in the field of industrialized production of 1,4-dibromo-2,5-diiodobenzene, can solve the difficulty of post-processing, increase the risk of industrial production, the difficulty of post-processing, and the reaction temperature High-level problems, to avoid the use of concentrated sulfuric acid, to facilitate industrial production, the effect of mild synthesis conditions

Active Publication Date: 2020-05-05
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A large amount of concentrated sulfuric acid is used in the synthesis process of the above two kinds of 1,4-dibromo-2,5-diiodobenzene. Concentrated sulfuric acid is a strong acid, which is dangerous in industrial production and difficult for post-processing.
In addition, the reaction temperature is higher when iodine is used for iodination, and 1,4-dibromobenzene is easy to sublime at high temperature. During the reaction, the raw materials are easy to sublimate on the wall of the reactor.
When periodate + potassium iodide is used for iodination, the reaction temperature is low, 1,4-dibromobenzene is difficult to dissolve, and the method is relatively complicated to operate, which greatly increases the risk of industrial production and the difficulty of post-processing

Method used

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  • Industrial production method of 1, 4-dibromo-2, 5-diiodobenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] A kind of industrialized production method of 1,4-dibromo-2,5-diiodobenzene, specifically comprises the following steps:

[0022] Add 3000mL of trifluoroacetic acid and 100.00g (423.89mmol) of 1,4-dibromobenzene to a 5000mL three-necked round-bottom flask in sequence, stir and raise the temperature to 68°C, and add 209.82g of N-iodosuccinimide in two times ( 932.56mmol), every interval of 2h, keep warm at 68°C for 20h, cool down to 20°C, add 3000mL of water to the system for dilution, filter, and recrystallize the filter cake with methylcyclohexane to obtain 148.39g of off-white solid, yield 71.78%. Such as Figure 1~3 as shown, 1 H NMR (500MHz, d 6 -DMSO): δ8.19(2H,s). 13 C NMR (500MHz, d 6 -DMSO): δ103.09, 129.02, 141.83. GC-MS: calcdfor C 6 h 2 Br 2 I 2 (M + ), 488; found, 488. This proves that 1,4-dibromo-2,5-diiodobenzene was successfully synthesized.

Embodiment 2

[0024] A kind of industrialized production method of 1,4-dibromo-2,5-diiodobenzene, specifically comprises the following steps:

[0025] Add 4000mL of trifluoroacetic acid and 100.00g (423.89mmol) of 1,4-dibromobenzene to a 5000mL three-necked round-bottom flask in sequence, stir and raise the temperature to 72°C, and add 190.73g of N-iodosuccinimide in two times ( 847.78mmol), every interval of 2h, keep warm at 72°C for 15h, cool down to 30°C, add 4000mL of water to the system for dilution, filter, and recrystallize the filter cake with methylcyclohexane to obtain 135.16g of off-white solid. The rate is 65.38%. GC-MS: calcd for C 6 h 2 Br 2 I 2 (M + ), 488; found, 488. 1 H NMR (500MHz, d 6 -DMSO): δ8.19(2H,s). 13 C NMR (500MHz, d 6 -DMSO): δ103.09, 129.02, 141.83.

Embodiment 3

[0027] A kind of industrialized production method of 1,4-dibromo-2,5-diiodobenzene, specifically comprises the following steps:

[0028] Add 2000mL of trifluoroacetic acid and 100.00g (423.89mmol) of 1,4-dibromobenzene to a 5000mL three-necked round-bottomed flask in sequence, stir and raise the temperature to 70°C, and add 247.95g of N-iodosuccinimide ( 1102.11mmol), every interval of 2h, keep warm at 70°C for 25h, cool down to 25°C, add 2000mL of water to the system for dilution, filter, and recrystallize the filter cake with methylcyclohexane to obtain 108.56g of off-white solid, yield 52.51%. 1 H NMR (500MHz, d 6 -DMSO): δ8.19(2H,s). 13 C NMR (500MHz, d 6 -DMSO): δ103.09, 129.02, 141.83. GC-MS: calcd for C 6 h 2 Br 2 I 2 (M + ), 488; found, 488.

[0029] Can obtain from above-mentioned Examples 1~3, compared with existing 1,4-dibromo-2,5-diiodobenzene synthetic method, the present invention adopts 1,4-dibromobenzene as raw material, in trifluoroacetic acid and Un...

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Abstract

The invention discloses an industrial production method of 1, 4-dibromo-2, 5-diiodobenzene, which belongs to the technical field of organic synthesis. The method comprises the step of carrying out iodination reaction at 68-72 DEG C under the action of trifluoroacetic acid and N-iodosuccinimide by using 1, 4-dibromobenzene as a raw material to obtain 1, 4-dibromo-2, 5-diiodobenzene. Compared with the existing 1, 4-dibromo-2, 5-diiodobenzene synthesis method, the method has the advantages that the use of concentrated sulfuric acid is avoided, the synthesis condition is mild, the operation is simple, the process is safe, and the industrial production is convenient.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an industrial production method of 1,4-dibromo-2,5-diiodobenzene. Background technique [0002] 1,4-dibromo-2,5-diiodobenzene contains two halogens, bromine and iodine, and the same halogens are para-positioned to each other, forming a completely symmetrical compound; halogens have high reactivity and can pass through such as Suzuki , Stille, Buchwald-Hartwig and other reactions to achieve chain segment growth. As a starting material, 1,4-dibromo-2,5-diiodobenzene is widely used in the synthesis of compounds with conjugated structures, and is widely used in solar cells, organic light-emitting diodes, field-effect transistors and other fields. [0003] At present, the synthesis methods of 1,4-dibromo-2,5-diiodobenzene all use 1,4-dibromobenzene as a raw material, and the specific synthesis methods are mainly divided into two types: 1) under the action of con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/12C07C25/02
CPCC07C17/12C07C25/02Y02P70/50
Inventor 李松松贾小伟毛涛王小伟
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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