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Method for preparing iodo-phenolic compounds

A phenolic compound and iodine technology is applied in the field of preparing iodinated phenolic compounds, can solve the problems of high price, complicated preparation of iodine donors and the like, and achieves the effects of low production cost, high use efficiency and high yield

Inactive Publication Date: 2008-12-10
ZHEJIANG QIMING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation of the iodine donor used in this type of method is cumbersome and expensive

Method used

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  • Method for preparing iodo-phenolic compounds

Examples

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Effect test

Embodiment 1

[0027] Embodiment 1 2, the preparation of 6-dimethyl p-iodophenol

[0028] In a 250 ml glass reactor equipped with a stirrer, 2,6-dimethylphenol (10 g, 82 mmol) and 150 ml of dry methanol were added, potassium iodide (13.6 g, 82 mmol) and sodium hydroxide (3.3 g, 82 mmol) was stirred at 0°C for 10 minutes, then slowly added dropwise a solution of 30 ml of methanol solution in which trichloroisocyanuric acid (6.4 g, 28 mmol) was dissolved, and the addition was completed within 45 minutes, and the temperature was maintained at 0°C After 0.5 hours of reaction, the reaction solution was poured into 500 milliliters of cold water, filtered, and the filter cake was washed with dry methanol, and the filtrate was adjusted to pH=5 with dilute hydrochloric acid. At this time, a large amount of solids were precipitated, filtered, and the filter cake was washed with water. After drying, 18.4 g of 2,6-dimethyl-p-iodophenol was obtained after recrystallization from ethyl acetate and petroleu...

Embodiment 2

[0029] Embodiment 2 2, the preparation of 6-dichloro-p-iodophenol

[0030]In a 100 ml glass reactor equipped with a stirrer, add 2,6-dichlorophenol (1 g, 6.1 mmol) and 30 ml dry methanol, add potassium iodide (1.02 g, 6.1 mmol) and sodium hydroxide (0.24 g , 6.1 mmol), after stirring at 0°C for 10 minutes, slowly dropwise added 10 ml of methanol solution dissolved with trichloroisocyanuric acid (0.48 g, 2.06 mmol), and the dropwise addition was completed within 15 minutes, and the temperature was maintained at 0°C , after 0.5 hours of reaction, pour the reaction solution into 200 ml of water, filter, wash the filter cake with dry methanol, adjust the pH=4 of the filtrate with dilute hydrochloric acid, at this time, a large amount of solids are precipitated, filter, wash the filter cake with water, and dry , to obtain 1.44 g of 2,6-dichloro-p-iodophenol (yield 81%).

Embodiment 3

[0031] Example 3 Preparation of 3-methoxyl-4-hydroxyl-5-iodo-benzaldehyde

[0032] 100 mL glass reactor, equipped with a stirrer, add vanillin (1.4 g, 9.2 mmol) and 30 mL of dry methanol, add potassium iodide (1.53 g, 9.2 mmol) and potassium hydroxide (0.52 g, 9.2 mmol) , after stirring at 0°C for 10 minutes, slowly add 10 ml of methanol solution in which trichloroisocyanuric acid (0.71 g, 3.1 mmol) was dissolved, dropwise within 15 minutes, keep the temperature at 0°C, and finish the reaction in 2 hours Finally, the reaction solution was poured into 200 ml of water, filtered, and the filter cake was washed with dry methanol. The filtrate was adjusted to pH=3 with dilute hydrochloric acid, extracted with ethyl acetate, concentrated, and recrystallized with ethyl acetate and petroleum ether to obtain 2.4 g 3-methoxy-4-hydroxy-5-iodo-benzaldehyde (96% yield).

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Abstract

The invention discloses a method for preparing an iodophenol compound, comprising the following steps of: dissolving the iodophenol compound in methanol, adding a strong base and potassium iodide with even stirring, dripping a methanol solution of a trichloroiminocyanuric acid, and carrying out separation and purification after the reaction stops completely to obtain the finished product. The molar ratio of the iodophenol compound to the strong base is between 1 to 1 and 1 to 2; the molar ratio of the iodophenol compound to the potassium iodide is between 1 to 1 and 1 to 2; the molar ratio of the iodophenol compound to the trichloroiminocyanuric acid is between 3 to 1 and 3 to 2. The method for preparing the iodophenol compound is nontoxic, free from pollution, low in price and production cost due to the use of the trichloroiminocyanuric acid as an oxidizer. The method also has the advantages of high utilization rate of iodine, good reaction selectivity, easy separation and purification of the finished product, and high yield.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing iodophenol compounds. Background technique [0002] Iodophenols are important organic compounds in organic synthesis and pharmaceutical intermediates. Under the catalysis of metal Pd, iodophenolic compounds can undergo Heck coupling reaction with terminal alkenes, Sonogashira reaction with terminal alkynes, and Stille coupling reaction with organotin to generate new carbon-carbon bonds; Diboration reagents react to form aryl borates. [0003] Iodophenolic compounds are generally prepared by the reaction of iodine donors and phenolic compounds. This reaction mainly occurs at the para-position and ortho-position of the phenolic hydroxyl group, wherein the structure of the phenolic compound is as shown in formula (I): [0004] [0005] Wherein R1 and R2 are the same or different, and can be one of the following substituents: H, C1-C4 alkyl, Cl, ...

Claims

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Application Information

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IPC IPC(8): C07C37/62C07C39/27C07C43/23C07C205/21
Inventor 刘学鹏王红亮张启明蔡明德姜申德
Owner ZHEJIANG QIMING PHARMA
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