A kind of preparation method of 1,3-dichloro-5-ethoxy-2-iodobenzene

A technology of ethoxy and iodobenzene is applied in the field of preparation of compound intermediates, and can solve the problems of low crystallization temperature, high energy consumption, and difficulty in obtaining, and achieve the effects of high yield and high product content.

Active Publication Date: 2018-05-22
TIANJIN CHENGJIAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is currently no literature report on this intermediate, but similar literature has reports on 1,3-dichloro-5-methoxy-2-iodobenzene, Chem.Eur.J.2013,19,4480–4495, expensive to use PhI(O 2 CCF 3 ) 2 For the reaction, the initial raw material 3,5-dichloroanisole is not easy to obtain, and the product contains 21% isomers; CN103012081 is initially prepared by iodization after etherification of trichlorophenyl, and the preparation process requires two steps Rectification, low crystallization temperature (-10 degrees) high energy consumption; Synthesis, (7), 1045-1054, 2011 adopts diazotization of sulfuric acid system, only 12% yield

Method used

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  • A kind of preparation method of 1,3-dichloro-5-ethoxy-2-iodobenzene
  • A kind of preparation method of 1,3-dichloro-5-ethoxy-2-iodobenzene
  • A kind of preparation method of 1,3-dichloro-5-ethoxy-2-iodobenzene

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Add 40ml of concentrated sulfuric acid (mass percentage concentration 98%, the same below) into a 100ml four-necked bottle equipped with a rotor, and add 6.6g of sodium nitrite in batches under controlled internal temperature of 5-10 degrees. Stir for 10 min after addition.

[0025] Add 20g of 1,3-dichloro-5-ethoxy-2-aminobenzene and 100ml of formic acid in sequence to a 500ml four-necked bottle equipped with mechanical stirring, control the internal temperature at 8-12 degrees, and slowly add the prepared After the sulfuric acid solution of sodium nitrite was added dropwise, the temperature was slowly raised to 25 degrees at room temperature, and stirred for 2 hours. Add 1.2g of urea, this is the diazotization reaction solution.

[0026] Add 40g of potassium iodide and 40ml of water into another 500ml four-necked bottle equipped with mechanical stirring, and add the diazotization reaction solution dropwise at an internal temperature of 20-25 degrees. Sodium bisulfate...

Embodiment 2

[0028] Add 10ml of concentrated sulfuric acid into a 25ml single bottle equipped with a rotor, and add 2.0g of sodium nitrite in batches at an internal temperature of 5-10 degrees. Stir for 10 min after addition.

[0029] Add 5.0g of 1,3-dichloro-5-ethoxy-2-aminobenzene, 25ml of formic acid and 25ml of propionic acid in sequence in a 100ml four-necked bottle equipped with mechanical stirring, control the internal temperature at 8-12 degrees, and slowly Add the prepared sulfuric acid solution of sodium nitrite, after the dropwise addition, slowly warm up to room temperature 25°C, stir for 2 hours, and add 0.4g of urea. This is the diazotization reaction solution.

[0030] Add 10g of potassium iodide and 10ml of water into another 500ml four-necked bottle equipped with mechanical stirring, and add the diazotization reaction solution dropwise at an internal temperature of 20-25 degrees. Sodium bisulfate in 100ml of ice water, extracted with dichloromethane, separated, and conce...

Embodiment 3

[0032] Add 20ml of concentrated sulfuric acid into a 50ml four-necked bottle equipped with a rotor, and add 3.75g of sodium nitrite in batches at an internal temperature of 5-10 degrees. Stir for 10 min after addition.

[0033] Add 10g of 1,3-dichloro-5-ethoxy-2-aminobenzene and 100ml of acetic acid in sequence to a 250ml four-necked bottle equipped with mechanical stirring, control the internal temperature at 8-12 degrees, and slowly add the prepared After the sulfuric acid solution of sodium nitrite was added dropwise, the temperature was slowly raised to 25 degrees at room temperature, and stirred for 2 hours. Add 0.6g of urea, this is the diazotization reaction solution.

[0034] Add 20g of potassium iodide and 20ml of water into another 250ml four-necked bottle equipped with mechanical stirring, and add the diazotization reaction solution dropwise at an internal temperature of 20-25 degrees. Add 2.5g of 200-300 mesh silica gel to reflux for 30 minutes after adding 15ml ...

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Abstract

The invention discloses a 1,3-dichloro-5-ethoxy-2-iodobenzene preparation method. The 1,3-dichloro-5-ethoxy-2-iodobenzene preparation method includes taking 1,3-dichloro-5-ethoxy-2-iodobenzene as a raw material and low-carbon-chain fatty acid as a solvent, diazotizing sodium nitrite dissolved by sulfuric acid, adding reaction liquid dropwise into a water solution like KI, adding sodium bisulfite solution to destroy excessive free iodine after reaction is completed, obtaining a crude product after extraction and concentration, using low-carbon-chain fatty alcohol for decoloration and crystallizing to obtain 1,3-dichloro-5-ethoxy-2-iodobenzene. The 1,3-dichloro-5-ethoxy-2-iodobenzene preparation method is available to raw materials, simple to operate and high in yield and purity.

Description

technical field [0001] The invention relates to a preparation method of a compound intermediate, especially a preparation method of 1,3-dichloro-5-ethoxy-2-iodobenzene. Background technique [0002] 1,3-Dichloro-5-ethoxy-2-iodobenzene is an important chemical intermediate. There is currently no literature report on this intermediate, but similar literature has reports on 1,3-dichloro-5-methoxy-2-iodobenzene, Chem.Eur.J.2013,19,4480–4495, expensive to use PhI(O 2 CCF 3 ) 2 For the reaction, the initial raw material 3,5-dichloroanisole is not easy to obtain, and the product contains 21% isomers; CN103012081 is initially prepared by iodization after etherification of trichlorophenyl, and the preparation process requires two steps Rectification, low crystallization temperature (-10 degrees) high energy consumption; Synthesis, (7), 1045-1054, 2011 adopts diazotization of sulfuric acid system, only 12% yield. Contents of the invention [0003] The technical problem to be so...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/22C07C43/225
CPCC07C41/22C07C43/225
Inventor 谷迎春费学宁林大勇李冉焦秀梅
Owner TIANJIN CHENGJIAN UNIV
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