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Preparation method of 2-bromo-5-iodophenol

A technology of iodophenol and iodoaniline, which is applied in the field of preparation of 2-bromo-5-iodophenol, and can solve problems such as difficult acquisition of raw materials

Inactive Publication Date: 2019-02-22
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, there is a method for the synthesis of the target compound. Yuki (PCT 2008123349) introduced a method of using 2-bromo-5-nitroanisole through reduction, diazotization, iodine, and demethylation to synthesize the target compound. , the yields of the three steps are 42%, 60% and 90% respectively, and the raw materials of this method are not easy to obtain

Method used

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  • Preparation method of 2-bromo-5-iodophenol

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Experimental program
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Effect test

Embodiment 1

[0018] (1) Iodine addition reaction: Add 100 g of o-nitroaniline and 1000 mL of solvent acetic acid into the reaction vessel. Stir, control the temperature at about 35 °C, and add 91 g of iodine in batches. After the addition, continue to stir, and GC traces until the end of the reaction. After the reaction was completed, 1000 mL of water was added, then neutralized with sodium hydroxide solution, allowed to cool, filtered with suction, and dried to obtain 180 g of light brown solid 2-nitro-4-iodoaniline, with a yield of 94%.

[0019] (2) Bromine reaction on diazo: Add 100 g of 2-nitro-4-iodoaniline to the reaction vessel, then add a solution made of 200 g of concentrated sulfuric acid and 400 mL of water, stir, and then dropwise add 37 g of A solution made of sodium nitrate and 120 mL of water was added, and the temperature was controlled at about 15 °C during the dropwise addition process. After the addition, stir for a period of time and prepare the diazonium salt for lat...

Embodiment 2

[0025] (1) Iodine addition reaction: Add 500 g of o-nitroaniline and 5200 mL of solvent acetic acid into the reaction vessel. Stir, control the temperature at about 40°C, and add 458 g of iodine in batches. After the addition, continue to stir, and GC traces until the end of the reaction. After the reaction was completed, 4000 mL of water was added, then neutralized with sodium hydroxide solution, allowed to cool, filtered with suction, and dried to obtain 930 g of 2-nitro-4-iodoaniline as a light brown solid with a yield of 97%.

[0026] (2) Bromination reaction on diazo: Add 600 g of 2-nitro-4-iodoaniline to the reaction vessel, then add a solution made of 1220 g of concentrated sulfuric acid and 2500 mL of water, stir, and then dropwise add 230 g of A solution made of sodium nitrate and 700 mL of water was added, and the temperature was controlled at about 15 °C during the dropwise addition process. After the addition, stir for a period of time and prepare the diazonium s...

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Abstract

The invention discloses an industrial preparation method of 2-bromo-5-iodophenol. According to the industrial preparation method of the 2-bromo-5-iodophenol, ortho-nitroaniline serves as an initial raw material, and the 2-bromo-5-iodophenol is synthesized by iodination, diazotization bromination, reduction and diazotization phenol hydroxylation four-step reaction. The 2-bromo-5-iodophenol obtainedin the process is blue solid with the purity of 97.5%, raw material conversion rate in each step reaches 100%, and the total yield of the whole process reaches 17%.

Description

technical field [0001] The present invention relates to a kind of production method of pharmaceutical intermediate, specifically, the present invention is a kind of preparation method of 2-bromo-5-iodophenol. Background technique [0002] At present, 2-bromo-5-iodophenol is mainly used in the pharmaceutical industry. For example, it can be used for: 1) Synthesis of trifluoromethylbenzyl alcohol compounds as regulators of transcription factors 2) Synthesis of pyridine derivatives that can inhibit TTK protease activity 3) Synthesis of N-phenyl-N'-benzenesulfonylpiperazine Derivative 4) for the synthesis of nanostructured compounds. [0003] At present, there is a method for the synthesis of the target compound. Yuki (PCT 2008123349) introduced a method of using 2-bromo-5-nitroanisole through reduction, diazotization, iodine, and demethylation to synthesize the target compound. , the yields of the three steps are 42%, 60% and 90% respectively, and the raw materials of this me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/27C07C37/00C07C211/52C07C209/74C07C205/12C07C201/12C07C209/32
CPCC07C37/002C07C201/12C07C209/325C07C209/74C07C211/52C07C205/12C07C39/27
Inventor 陈兴权董燕敏
Owner CHANGZHOU UNIV
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