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A kind of preparation method of 2-fluoro-6-nitroaniline

A technology of nitroaniline and fluoronitrobenzene, which is applied in the field of preparation of 2-fluoro-6-nitroaniline, can solve the problems of unfavorable scale-up production, poor nitrification selectivity, and a large amount of waste water, and achieve low price, little pollution, tractable effect

Active Publication Date: 2022-03-11
无锡双启科技有限公司
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  • Description
  • Claims
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Problems solved by technology

[0004] In the above-mentioned synthetic method, in the process of synthesizing 2-fluoro-6-nitroaniline compound I, the first step reaction uses precursor acetic anhydride, and the second step reaction uses precursor nitric acid, and simultaneously due to nitration selection Poor performance, resulting in low yield, and a large amount of waste water, which is not conducive to industrial scale-up production

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  • A kind of preparation method of 2-fluoro-6-nitroaniline
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  • A kind of preparation method of 2-fluoro-6-nitroaniline

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Embodiment 1

[0020] A preparation method of 2-fluoro-6-nitroaniline, said preparation method comprising the steps of:

[0021] (1) Add 14.1g (100mmol) m-fluoronitrobenzene, 20g (250mmol) lithium tert-butoxide, 47.3g (200mmol) hexachloroethane, 100ml N,N-dimethylformamide, add After heating up to 70°C and stirring for 4 hours, follow the reaction by HPLC until the reaction of m-fluoronitrobenzene is complete; add 300ml of ethyl acetate, wash the organic layer with 1M hydrochloric acid, then wash with saturated sodium chloride, concentrate the organic layer, and recrystallize from toluene to obtain 13g of Compound III, molar yield: 74.3%.

[0022] (2) Add 100ml N,N-dimethylformamide, 8.75g (50mmol) of compound III to the autoclave, pass through 4.25g (250mmol) of ammonia gas, heat up to 70°C and stir for 6 hours, follow the reaction by HPLC until the compound The reaction of III was complete; the reaction solution was concentrated and recrystallized from ethanol water system to obtain 6.24 ...

Embodiment 2

[0026] A preparation method of 2-fluoro-6-nitroaniline, said preparation method comprising the steps of:

[0027] (1) Add 14.1g (100mmol) m-fluoronitrobenzene, 24g (300mmol) lithium tert-butoxide, 47.3g (200mmol) hexachloroethane, 100ml N,N-dimethylformamide, add After heating up to 60°C and stirring for 2 hours, follow the reaction by HPLC until the reaction of m-fluoronitrobenzene is complete; add 300ml of ethyl acetate, wash the organic layer with 1M hydrochloric acid, then wash with saturated sodium chloride, concentrate the organic layer, and recrystallize from toluene to obtain 13.3g Compound III, molar yield: 76%.

[0028] (2) Add 100ml dimethyl sulfoxide, 8.75g (50mmol) of compound III to the autoclave, pass through 8.5g (500mmol) of ammonia gas, heat up to 40°C and stir for 8 hours, and follow the reaction by HPLC until the reaction of compound III is complete; The solid was forced out with 300ml of water, filtered, and the crude product was recrystallized with an et...

Embodiment 3

[0030] A preparation method of 2-fluoro-6-nitroaniline, said preparation method comprising the steps of:

[0031] (1) Add 14.1g (100mmol) m-fluoronitrobenzene, 20g (250mmol) lithium tert-butoxide, 47.3g (200mmol) hexachloroethane, 100ml N,N-dimethylformamide, add Completely raise the temperature to 50°C and stir for 6 hours, follow the reaction by HPLC until the reaction of m-fluoronitrobenzene is complete; add 300ml of ethyl acetate, wash the organic layer with 1M hydrochloric acid, then wash with saturated sodium chloride, concentrate the organic layer, and recrystallize from toluene to obtain 12.8g Compound III, molar yield: 73.1%.

[0032] (2) Add 100ml of ethanol, 8.75g (50mmol) of compound III, 9.3g (150mmol) of 28% ammonia water in the autoclave, heat up to 100°C and stir for 12 hours, follow the reaction by HPLC until the reaction of compound III is complete; concentrate the reaction solution, Recrystallization from ethanol water system gave 5.07 g of compound I, mola...

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Abstract

The invention discloses a preparation method of 2-fluoro-6-nitroaniline. The specific steps of the preparation method are: (1) using m-fluoronitrobenzene as a starting material, under the catalytic condition of lithium tert-butoxide React with hexachloroethane to generate compound III; (2) aminolyze compound III to generate compound I; that is, the 2-fluoro-6-nitroaniline. The present invention avoids a large number of precursors to poison and explosives during the total synthesis route using m-fluoronitrobenzene as the starting material, and at the same time, the price of raw materials is low, so that the whole synthesis process is not only less polluting, easy to handle, but also has a higher yield. high.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a preparation method of 2-fluoro-6-nitroaniline. Background technique [0002] 2-fluoro-6-nitroaniline is a class of key intermediates, and Journal of Fluorine Chemistry, 1989, vol.42, p.245-256 discloses the following route for the synthesis of 2-fluoro-6-nitroaniline compound I: [0003] [0004] In the above-mentioned synthetic method, in the process of synthesizing 2-fluoro-6-nitroaniline compound I, the first step reaction uses precursor acetic anhydride, and the second step reaction uses precursor nitric acid, and simultaneously due to nitration selection Poor performance leads to low yield and produces a large amount of waste water, which is not conducive to industrial scale-up production. Contents of the invention [0005] In view of the above-mentioned problems in the prior art, the applicant of the present invention provides a preparation me...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/10C07C211/52
CPCC07C209/10C07C201/12C07C211/52C07C205/12
Inventor 张国强王昌军秦英
Owner 无锡双启科技有限公司
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