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Synthesis method of 1, 4-dimethoxy tetrafluorobenzene

A technology of dimethoxytetrafluorobenzene and dimethylpentafluoroaniline, which is applied in the field of synthesis of 1,4-dimethoxytetrafluorobenzene, can solve the problems of long reaction time, unfavorable industrial production, low yield, etc. problem, to achieve the effects of simple post-processing, improved anti-overcharge performance, and mild reaction conditions

Active Publication Date: 2021-07-09
ZHANGJIAGANG GUOTAI HUARONG NEW CHEM MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Document J.Am.Chem.Soc.1997,119,12503. discloses the method that adopts tetrafluorohydroquinone and methyl iodide reaction to prepare 1,4-dimethoxytetrafluorobenzene in the report, and this method reaction time is long Up to 3 days, low yield (2%)
[0008] In summary, the above-mentioned synthetic methods of 1,4-dimethoxytetrafluorobenzene all have relatively large limitations, which are unfavorable for industrialized production

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  • Synthesis method of 1, 4-dimethoxy tetrafluorobenzene
  • Synthesis method of 1, 4-dimethoxy tetrafluorobenzene
  • Synthesis method of 1, 4-dimethoxy tetrafluorobenzene

Examples

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Embodiment 1

[0039] Add N,N-dimethylpentafluoroaniline (211.1g, 1.0mol) into a 2L three-necked flask equipped with a stirrer, a thermometer, and a condenser tube, and add a 30% methanol solution of sodium methoxide (198g, containing Sodium methoxide (1.1mol) was added dropwise to the reaction system—N,N-dimethylpentafluoroaniline. After the dropwise addition, the reflux reaction was carried out for 6 hours. After the reaction was completed, the reaction solution was filtered, and 200g of ethyl acetate was added to obtain an organic Washing with 200g of deionized water, liquid separation, washing and liquid separation cycle 3 times, the obtained organic phase was decompressed and desolvated by a rotary evaporator, and then rectified to obtain 178.3g of intermediate I.

[0040] Intermediate I (133.9g, 0.6mol) and acetonitrile (300g) were respectively added to a 1L three-necked flask equipped with a stirrer, a thermometer, and a condenser, and methyl trifluoromethanesulfonate (108.3g, 0.66mol)...

Embodiment 2

[0044] Add N,N-dimethylpentafluoroaniline (211.1g, 1.0mol) into a 2L three-necked flask equipped with a stirrer, a thermometer, and a condenser tube, and add a 30% methanol solution of sodium methoxide (234g, containing The mixed solution of sodium methoxide (1.3mol) and 200g of acetonitrile was added dropwise to the reaction system. After the dropwise addition, the reflux reaction was carried out for 8h. After the reaction was completed, the reaction solution was filtered, and 200g of ethyl acetate was added. Washing and liquid separation were performed 3 times in total. The obtained organic phase was decompressed by a rotary evaporator to remove the solvent, and then rectified to obtain 190.5 g of intermediate I.

[0045] Intermediate I (133.9g, 0.6mol) and acetonitrile (300g) were respectively added to a 1L three-necked flask equipped with a stirrer, a thermometer, and a condenser, and methyl trifluoromethanesulfonate (128.0g, 0.78mol) was added dropwise, After the dropwise...

Embodiment 3

[0048] Add N,N-dimethylpentafluoroaniline (211.1g, 1.0mol) into a 2L three-necked flask equipped with a stirrer, a thermometer, and a condenser tube, and add a 30% methanol solution of sodium methoxide (234g, containing The mixed solution of sodium methoxide (1.3mol) and 200g of acetonitrile was added dropwise to the reaction system. After the dropwise addition, the reflux reaction was carried out for 8h. After the reaction was completed, the reaction solution was filtered, and 200g of ethyl acetate was added. Washing, liquid separation, a total of 3 times, the obtained organic phase was decompressed by a rotary evaporator to remove the solvent, and then rectified to obtain intermediate I190.5g.

[0049] Intermediate I (133.9g, 0.6mol) and acetonitrile (300g) were respectively added to a 1L three-necked flask equipped with a stirrer, a thermometer, and a condenser, and methyl trifluoromethanesulfonate (128.0g, 0.78mol) was added dropwise, After the dropwise addition, the tempe...

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Abstract

The invention discloses a synthesis method of 1, 4-dimethoxy tetrafluorobenzene, the synthesis method comprises the following steps: (1) reacting N, N-dimethyl pentafluoroaniline with sodium methoxide to obtain an intermediate I; (2) mixing the intermediate I with a first organic solvent, and then reacting with methyl trifluoromethanesulfonate to obtain an intermediate II; and (3) mixing the intermediate II with a second organic solvent, and reacting with methanol in alkali and protective gas atmosphere to obtain the 1, 4-dimethoxy tetrafluorobenzene. The synthesis method of the 1, 4-dimethoxy tetrafluorobenzene has the advantages of mild reaction conditions, no need of harsh conditions, high controllability, simple post-treatment, easiness in operation, capability of effectively improving the overcharge resistance of the lithium ion battery and the like.

Description

technical field [0001] The invention relates to the technical field of organic synthesis chemistry, in particular to a synthesis method of 1,4-dimethoxytetrafluorobenzene. Background technique [0002] Rechargeable lithium-ion batteries are widely used in business. In the "blood" of lithium-ion batteries—electrolyte, fluorinated aromatic hydrocarbons and fluorinated aryl ether compounds are used as functional additives for lithium-ion batteries, which play a role in preventing overcharge of lithium-ion batteries. play a vital role. [0003] 1,4-Dimethoxytetrafluorobenzene is one of the fluorine-containing aromatic ethers. The common synthetic methods for synthesizing 1,4-dimethoxytetrafluorobenzene are as follows: [0004] Literature Nature, 1956,178,199. discloses the method for preparing 1,4-dimethoxytetrafluorobenzene by refluxing hexafluorobenzene in methanol solution of sodium methoxide, which is easy to generate ortho, meta and para A mixture of isomers, and a small ...

Claims

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Application Information

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IPC IPC(8): C07C41/01C07C43/225
CPCC07C41/01C07C213/00C07C43/225C07C217/84
Inventor 印李达时二波吕鹏程陈明凯刘栋成陶力周铭柯
Owner ZHANGJIAGANG GUOTAI HUARONG NEW CHEM MATERIALS CO LTD
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