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Synthesis method of fluorine-substituted naphthol

A synthetic method, naphthol technology, applied in the field of organic synthesis, can solve the problems of poor control of the reaction process, harsh reaction conditions, and long reaction routes, and achieve the effects of mild reaction conditions, reduced equipment investment, and reduced production costs

Inactive Publication Date: 2012-09-05
ZHEJIANG BOTAI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] The reaction process in method (1) is not easy to control, especially when brominated, it is easy to produce more by-products
[0016] In the method (2), there are problems that the reaction route is relatively long and the reaction conditions are harsh, and the expensive fluorinated reagent 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane is used. Alkane di(tetrafluoroborate) salt (F-TEDA-BF4) and diethylaminosulfur trifluoride (DAST)

Method used

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  • Synthesis method of fluorine-substituted naphthol
  • Synthesis method of fluorine-substituted naphthol
  • Synthesis method of fluorine-substituted naphthol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Dissolve 200g of 2,3-difluorophenylacetic acid in 800ml of 1,2-dichloroethane solvent, add 5g of DMF and 190g of thionyl chloride, heat to 70°C for 3-4 hours, concentrate to dryness, and cool to After 25°C, it can be used for the next step of cyclization reaction.

[0047] Dissolve the 2,3-difluorophenylacetyl chloride obtained in the previous step with 100ml of 1,2-dichloroethane and cool to -15°C, keep the temperature, slowly add 154g of anhydrous aluminum chloride, and react for 2 hours , feed ethylene and raise the temperature to 5°C, and continue feeding ethylene for 2 hours until basically no ethylene is absorbed. The reaction solution was poured into 80ml of water and stirred for 10 minutes, and the layers were separated. The aqueous layer was extracted with dichloromethane. The organic phases were combined, washed with saturated brine, and concentrated under reduced pressure to obtain an oily substance for the next rearrangement reaction.

[0048] Dissolve the ...

Embodiment 2

[0050] Dissolve 200g of 2,3-difluorophenylacetic acid in 800ml of dichloromethane solvent, add 8g of pyridine and 190g of thionyl chloride, heat at 50°C for 7-8 hours, and cool to 25°C for the next step of cyclization reaction.

[0051] Cool the dichloromethane solution of 2,3-difluorophenylacetyl chloride obtained in the previous step to -5°C, keep the temperature, slowly add 247g of ytterbium trifluoromethanesulfonate, react for 2 hours, pass through ethylene and raise the temperature to 50°C, and continue to pass ethylene for 2 hours until basically no ethylene is absorbed. The reaction solution was poured into 80ml of water and stirred for 10 minutes, and the layers were separated. The aqueous layer was extracted with dichloromethane. The organic phases were combined, washed with saturated brine, and concentrated under reduced pressure to obtain an oily substance for the next rearrangement reaction.

[0052] Dissolve the oil obtained in the previous reaction in 3000ml of ac...

Embodiment 3

[0054] Dissolve 200g of 3,4,5-trifluorophenylacetic acid in 800ml of 1,2-dichloroethane solvent, add 15g of DMF and 113g of oxalyl chloride, heat to 90°C for 3-4 hours, concentrate to dryness, and cool to 25 ℃ can be used for the next step of the cyclization reaction.

[0055] Dissolve the 3,4,5-trifluorophenylacetyl chloride obtained in the previous step reaction with 100ml 1,2-dichloroethane and cool to -15°C, keep the temperature, slowly add 190g anhydrous aluminum chloride, and react After 2 hours, feed ethylene and raise the temperature to 25°C, and continue feeding ethylene for 2 hours until basically no ethylene is absorbed. The reaction solution was poured into 80ml of water and stirred for 10 minutes, and the layers were separated. The aqueous layer was extracted with dichloromethane. The organic phases were combined, washed with saturated brine, and concentrated under reduced pressure to obtain an oily substance for the next rearrangement reaction.

[0056] Dissolve...

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Abstract

The invention relates to a synthesis method of fluorine-substituted naphthol. In the method, phenylacetic acid is halogenated by acyl, cyclized by ethylene and then rearranged to obtain a compound of the formula (I). The synthesis method has simple step, moderate reaction condition and low cost.

Description

technical field [0001] The invention relates to an organic synthesis method, in particular to a synthesis method of fluorine-substituted naphthol. Background technique [0002] Fluorine-substituted naphthol is an intermediate that can be used in pesticides, medicines and liquid crystal display element materials. Its general structural formula (I) is as follows: [0003] [0004] Among them, R 1 , R 2 , R 3 , R 4 For fluorine or hydrogen. [0005] The synthetic method of the fluorine-substituted naphthol disclosed in the prior art has following several kinds at present: [0006] (1) Chinese patent CN 1684933A (disclosure date: 2005-10-19) discloses the preparation method of 1,7,8-trifluoro-2-naphthol and its liquid crystal compound, wherein 7,8-difluoro- The preparation method of 2-naphthol is to prepare 7,8-difluoro-1,2,3 by reacting with ethylene in the presence of anhydrous aluminum chloride after making 2,3-difluorophenylacetic acid into acid chloride , 4-tetra...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/38C07C37/07B01J31/02
Inventor 童华光王敏吴丽燕张奇方高飞张荣
Owner ZHEJIANG BOTAI CHEM
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