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Preparation method of 2-fluoro-4,5-dichloronitrobenzene

A kind of technology of dichloronitrobenzene and fluoroaniline, which is applied in the field of preparation of medicine and pesticide intermediates

Active Publication Date: 2012-11-28
JINING XINRUIDA INFORMATION TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But do not see the report that its synthetic method is arranged at present, therefore, it is very necessary to develop a synthetic route

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (1) Acetylation and chlorination in one pot: add 22.2 g of freshly distilled p-fluoroaniline and 60 mL of glacial acetic acid to the reaction vessel, raise the temperature to 30 °C, and add 20.4 g of acetic anhydride drop by drop while stirring. After the acetic anhydride is dropped, heat to 60-70 °C, and keep the temperature until the end of the reaction. Slightly lower the temperature to 40 °C, slowly introduce Cl 2 , maintain the reaction temperature at 40-50 °C, keep the reaction for 12 h, and the reaction ends. Pour the product into 500 mL of ice water, precipitate solids, filter with suction, and use Na 2 CO 3 Adjust to neutral and then filter to obtain crude product. After recrystallization from 60% ethanol aqueous solution, 29.8 g of white needle-like solid 2-chloro-4-fluoroacetanilide was obtained with a yield of 79.1%.

[0021] (2) Hydrolysis reaction: Add 28.1 g of 2-chloro-4-fluoroacetanilide into the reaction vessel, slowly add 12.0 g of NaOH and 108 g ...

Embodiment 2

[0026] (1) Acetylation and chlorination in one pot: Add 22.2 g of freshly distilled p-fluoroaniline and 60 mL of glacial acetic acid to the reaction vessel, heat up to 70 °C, and add 30.6 g of acetic anhydride drop by drop while stirring. After the acetic anhydride is dripped, heat to 90-100 °C, and keep warm until the reaction is completed. Slightly lower the temperature to 60 °C, slowly introduce Cl 2 , maintain the reaction temperature at 50-60 °C, keep the reaction for 10 h, and the reaction ends. Pour the product into 500 mL of ice water, precipitate solids, filter with suction, and use Na 2 CO 3 Adjust to neutral and then filter to obtain crude product. After recrystallization from 80% ethanol aqueous solution, 30.0 g of white needle-like solid 2-chloro-4-fluoroacetanilide was obtained with a yield of 79.7%.

[0027] (2) Hydrolysis reaction: Add 28.1 g of 2-chloro-4-fluoroacetanilide into the reaction vessel, slowly add 18.0 g of NaOH and 162 g of H 2 O mixed into a...

Embodiment 3

[0032] (1) Acetylation and chlorination in one pot: Add 55.5 g of freshly distilled p-fluoroaniline and 160 mL of glacial acetic acid to the reaction vessel, heat up to 40 °C, and add 59.2 g of acetic anhydride drop by drop while stirring. After the acetic anhydride is dropped, heat it to 70-80 °C, and keep it warm until the reaction ends. Slightly lower the temperature to 40 °C, slowly introduce Cl 2 , maintain the reaction temperature at 40-50 °C, keep the reaction for 13.5 h, and the reaction ends. Pour the product into 1500 mL of ice water, precipitate solids, filter with suction, and use Na 2 CO 3 Adjust to neutral and then filter to obtain crude product. After recrystallization from 70% ethanol aqueous solution, 78.8 g of white needle-like solid 2-chloro-4-fluoroacetanilide was obtained, with a yield of 83.5%.

[0033] (2) Hydrolysis reaction: Add 28.1 g of 2-chloro-4-fluoroacetanilide into the reaction vessel, slowly add 14.4 g of NaOH and 129.6 g of H 2 O mixed in...

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PUM

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Abstract

The invention discloses a preparation method of 2-fluoro-4,5-dichloronitrobenzene, relating to the technical field of preparation of medicine and pesticide intermediates. The industrialized preparation method of the 2-fluoro-4,5-dichloronitrobenzene comprises the following steps: by using 4-fluoroaniline as an initial raw material, carrying out acetylation, chlorination, hydrolysis, diazotization-Sandmeyer reaction and nitrification to synthesize the 2-fluoro-4,5-dichloronitrobenzene. The 2-fluoro-4,5-dichloronitrobenzene prepared by the method disclosed by the invention is a light yellow solid, and the purity is 98.5%; the raw material conversion rate for each reaction step reaches 100%; and the total yield of the whole process is up to 27.1%.

Description

technical field [0001] The invention relates to the technical field of preparation of medicine and pesticide intermediates, in particular, the invention is a preparation method of 2-fluoro-4,5-dichloronitrobenzene. Background technique [0002] 2-Fluoro-4,5-dichloronitrobenzene, as an important medicine and pesticide intermediate, has a wide range of uses, such as the synthesis of 1) dibenzocycloheptene derivatives, which can treat nervous disorders. (Ek Fredyik, Olsson Roger, Ohlsson Jorgen. Amino-substituted diaryl[a,d]cycloheptene analogs as for preparing them, and their use as muscarinic agonists[P]. WO 2008021463 A2, 2008-02-21); 2) have Benzenesulfonamide and benzimidazole derivatives with antimicrobial properties. (Brooks Carl, Goodman Krista B, Cleary Pamela A, et al. Benzenesulfonamide inhibitor of CCR2 chemokine receptor[P]. WO 2007014054 A2, 2007-02-01); 3) Quinazoline derivatives can effectively inhibit protein tyrosinase The activity of amino acid kinase can r...

Claims

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Application Information

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IPC IPC(8): C07C205/12C07C201/08
Inventor 陈兴权蒋锐董燕敏郝永兵王林殷杰
Owner JINING XINRUIDA INFORMATION TECH CO LTD
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