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Preparation method of 1-iododibenzofuran

A technology of nitrodibenzofuran and aminodibenzofuran, which is applied in the field of preparation of 1-iododibenzofuran, can solve the problems of high synthesis cost, many reaction raw materials, long reaction time, etc., and achieve stable yield , The synthesis method is simple and easy, and the effect of little pollution

Pending Publication Date: 2019-07-23
SUZHOU SY PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing synthesis method of 1-iododibenzofuran has the problems of cumbersome operation and long reaction time, and there are many reaction raw materials and high synthesis cost, and some steps require ultra-low temperature reaction

Method used

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  • Preparation method of 1-iododibenzofuran

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Embodiment 1

[0023] A preparation method of 1-iododibenzofuran, comprising the following steps:

[0024] S1. In a 500mL round bottom flask, add dimethyl ether (66.4mL), potassium tert-butoxide (13.3g, 0.119mol), cuprous iodide (11.32g, 0.058mol), replace with nitrogen three times, and stir for 1h , Dissolve m-dinitrobenzene (6.64g, 0.039mol) with pyridine (66.4mL), add it into a round bottom flask, and stir for 1h, potassium tert-butoxide (5.3g, 0.047mol) and o-iodophenol (10g, 0.045mol) was dissolved with dimethyl ether (20mL), the temperature needs to be controlled below 10°C, and then added to the system, after nitrogen replacement, the external temperature was set to 100°C, and the reaction was carried out for 7 hours. Use a spot plate to observe the completion of the reaction, and then add 1mol / L hydrochloric acid After washing with water and suction filtration, the filtrate was extracted with dimethyl ether (65mL), concentrated to 10mL, petroleum ether (10mL) was added, silica gel (1...

Embodiment 2

[0028] A preparation method of 1-iododibenzofuran, comprising the following steps:

[0029] S1. In a 100L reactor, add dimethyl ether (13.28L), potassium tert-butoxide (2.66Kg, 23.72mol), cuprous iodide (2.25Kg, 11.86mol), nitrogen replacement three times, and stir for 1h. Dissolve m-dinitrobenzene (1.33Kg, 7.91mol) with pyridine (13.3L), add to the reaction kettle, stir for 1h, potassium tert-butoxide (1.064Kg, 9.49mol) and o-iodophenol (2Kg, 9.09mol ) is dissolved in dimethyl ether (6.63L), and the temperature needs to be controlled below 10°C, and then added to the system. After nitrogen replacement, the external temperature is set to 100°C, and the reaction is carried out for 7 hours. Use a spot plate to observe the completion of the reaction, and then add 1mol / L hydrochloric acid to wash. , after suction filtration, the filtrate was extracted with dimethyl ether (13L), concentrated to 2L, and petroleum ether (2L) was added, and then silica gel (1Kg) was added for adsorpti...

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Abstract

The invention provides a preparation method of 1-iododibenzofuran. The preparation method comprises the following steps: adding potassium tert-butoxide, dimethyl ether and cuprous iodide into a firstreactor, stirring the mixture under the protection of nitrogen gas, adding m-dinitrobenzene dissolved with pyridine into a system, then dissolving potassium tert-butoxide and o-iodophenol with dimethyl ether, adding the dissolved mixture into the system, fully reacting under the protection of the nitrogen gas, and separating to obtain 1-nitryldibenzofuran; then adding 1-nitryldibenzofuran into a second reactor, adding ethanol, water, iron powder and ammonium chloride, fully reacting, and separating to obtain 1-aminodibenzofuran; adding the 1-aminodibenzofuran into a third reactor, then addinghydrochloric acid, dropwise adding a sodium nitrite solution and a KI solution, fully reacting, and separating to obtain 1-iododibenzofuran. The preparation method has the beneficial effects of avoidance of carrying out the reactions under an ultralow temperature reaction condition, simple and feasible synthetic method, stable productivity, higher yield and low pollution, and has remarkable advantages on the aspect of batch production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 1-iododibenzofuran. Background technique [0002] Dibenzofuran and its derivatives have unique structures and novel properties, making them important precursors in synthetic chemistry. At present, the synthetic chemistry of dibenzofuran as a parent is an important hotspot in modern organic synthesis. These Derivatives can be widely used in medicine, pesticides, physical chemistry, material chemistry and life sciences, and have very good development and application prospects. 1-Iododibenzofuran is an important derivative of dibenzofuran, which makes it useful in the synthesis of OLED materials and in the synthesis of molecular machines and pharmaceutical intermediates, greatly expanding the development of carbazole as the parent structure. The application prospect of the compound. The existing synthesis method of 1-iododibenzofuran has the probl...

Claims

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Application Information

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IPC IPC(8): C07D307/91
CPCC07D307/91
Inventor 姚梁锋
Owner SUZHOU SY PHARMA TECH CO LTD
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