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A kind of preparation method of 5-arylsulfonyl-2-chlorophenol compound

A technology for arylsulfonyl and compound, which is applied in the field of preparation of 5-arylsulfonyl-2-chlorophenol compounds, can solve the problems of many reaction by-products, difficulty in synthesis, non-compliance with positioning rules, etc. The effect of mild reaction conditions

Inactive Publication Date: 2018-06-08
ANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is difficult to synthesize by traditional electrophilic substitution of aromatic compounds during its preparation. Not only do the substituents need to be introduced gradually, but some do not conform to the positioning rules, and there are many reaction by-products.

Method used

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  • A kind of preparation method of 5-arylsulfonyl-2-chlorophenol compound
  • A kind of preparation method of 5-arylsulfonyl-2-chlorophenol compound
  • A kind of preparation method of 5-arylsulfonyl-2-chlorophenol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 359 mg (1 mmol) of 2-(5-p-toluenesulfonyl-2-chlorophenoxy)pyridine, 328 mg (2 mmol) of methyl trifluoromethanesulfonate, and 10 mL of toluene into the reaction tube. Under nitrogen, 100 o C stirred for 24 hours. After the reaction, the crude product was separated, then added to the reaction tube, added sodium metal (15mmol) and methanol (15mL), refluxed for 15 minutes, cooled, and separated by column chromatography to obtain the target product 5-p-toluenesulfonyl -2-Chlorophenol, the yield is 74%.

Embodiment 2

[0018] Add 345 mg (1 mmol) of 2-(5-benzenesulfonyl-2-chlorophenoxy)pyridine, 328 mg (2 mmol) of methyl trifluoromethanesulfonate, and 10 mL of toluene to the reaction tube. Under nitrogen, 100 o C stirred for 24 hours. After the reaction, the crude product was separated, then added to the reaction tube, added sodium metal (15mmol) and methanol (15mL), refluxed for 15 minutes, cooled, and separated by column chromatography to obtain the target product 5-benzenesulfonyl- 2-Chlorophenol, yield 73%.

Embodiment 3

[0020] Add 395 mg (1 mmol) of 2-(5-(2-naphthalenesulfonyl)-2-chlorophenoxy)pyridine, 328 mg (2 mmol) of methyl trifluoromethanesulfonate, 10 mL of toluene, and nitrogen into the reaction tube condition, 100 o C stirred for 24 hours. After the reaction, the crude product was separated, then added to the reaction tube, added sodium metal (15mmol) and methanol (15mL), refluxed for 15 minutes, cooled, and separated by column chromatography to obtain the target product 5-(2-naphthalene Sulfonyl)-2-chlorophenol, the yield was 77%.

[0021] The following table is the synthetic product and the corresponding productive rate adopting the technical scheme of the present invention:

[0022]

[0023] Note: p-tosyl in the table is p-toluenesulfonyl.

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Abstract

The invention discloses a preparation method of a 5-arylsulfonyl-2-chlorophenol compound, which is prepared from a 2-(5-arylsulfonyl-2-chlorophenoxy) pyridine compound as a raw material by the following steps: A: directly adding the 2-(5-arylsulfonyl-2-chlorophenoxy) pyridine compound, methyl trifluoromethansulfonate and toluene into a reacting device, stirring for reacting for 24 hours at 100 DEG C, and then separating a crude product; and B: adding the crude product obtained in the step A to methanol, adding sodium, refluxing for 15 minutes, and separating to obtain the 5-arylsulfonyl-2-chlorophenol compound. The preparation method is simple and mild in reaction conditions, is finished in one step, and can be well applied to preparation of the 5-arylsulfonyl-2-chlorophenol compound.

Description

technical field [0001] The invention relates to a preparation method of 5-arylsulfonyl-2-chlorophenol compounds, belonging to the field of chemistry. Background technique [0002] 5-Arylsulfonyl-2-chlorophenol compounds are a class of important structural units, which are widely used in the synthesis of drugs, pesticides and natural products. It is difficult to synthesize by using the traditional electrophilic substitution of aromatic compounds during its preparation. The substituents not only need to be gradually introduced, but also some do not conform to the positioning rules, and there are many reaction by-products. Contents of the invention [0003] The object of the present invention is to overcome the problem that traditional 5-arylsulfonyl-2-chlorophenol compounds are difficult to synthesize, and to provide a preparation method of 5-arylsulfonyl-2-chlorophenol compounds. [0004] For realizing the purpose of the present invention, adopted following technical schem...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/643C07C315/04C07C317/22
CPCC07C315/04C07D213/643C07C317/22
Inventor 李刚杨素玲赵丰吕允贺王亚
Owner ANYANG NORMAL UNIV
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