A kind of preparation method of 2-(5-fluoro-2,4-dinitrophenoxy)acetic acid
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A technology of dinitrophenoxy and dinitrobenzene, which is applied in the field of preparation of 2-acetic acid, can solve the problems of high production cost, high price, unfavorable commercial production, etc., and achieve short reaction time, less waste, and post-treatment simple effect
Active Publication Date: 2022-04-26
内蒙古世杰化工有限公司
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[0012] Although this method has a short route, expensive glycolic acid needs to be used in the preparation process of the raw material dicyclohexyl ammonium glycolate, and the production cost is high, which is not conducive to commercial production
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Embodiment 1
[0027] Add 6.12g of 1,5-difluoro-2,4-dinitrobenzene, 15mL of ethylene glycol, and 3.03g of triethylamine into the reactor, and react at room temperature for 2.5h. After the reaction, add 20ml of water, extract with 50ml of toluene, wash the organic layer once with 20ml of water, collect the organic phase and obtain 2-(5-fluoro-2,4-dinitrophenoxy)ethanol with a yield of 84% ; 1 H NMR (500MHz, CDCl 3 )δ8.81(d, J=7.8Hz, 1H), 7.04(d, J=11.9Hz, 1H), 4.44–4.29(m, 2H), 4.08(dt, J=5.8, 4.6Hz, 2H), 2.40 (t, J=6.3Hz, 1H).
Embodiment 2
[0029] Add 10.2g of 1,5-difluoro-2,4-dinitrobenzene, 14mL of ethylene glycol, and 4.24g of anhydrous sodium carbonate into the reactor, and react at room temperature for 3h. After the reaction, add 30ml of water, extract with 55ml of toluene, wash the organic layer once with 20ml of water, collect the organic phase and obtain 2-(5-fluoro-2,4-dinitrophenoxy)ethanol with a yield of 86% .
Embodiment 3
[0031] Add 12.2g of 1,5-difluoro-2,4-dinitrobenzene, 23mL of ethylene glycol, and 5.05g of triethylamine into the reactor, and react at room temperature for 2h. After the reaction, add 35ml of water, extract with 55ml of toluene, wash the organic layer once with 30ml of water, collect the organic phase and obtain 2-(5-fluoro-2,4-dinitrophenoxy)ethanol with a yield of 85% .
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Abstract
The invention discloses a preparation method of 2-(5-fluoro-2,4-dinitrophenoxy)acetic acid. The preparation method comprises: using 1,5-difluoro-2,4-dinitrobenzene and ethylene glycol as raw materials, reacting under the action of a base to obtain 2-(5-fluoro-2,4-dinitrobenzene Oxygen) ethanol, 2-(5-fluoro-2,4-dinitrophenoxy)ethanol is oxidized under the action of an oxidizing agent to obtain 2-(5-fluoro-2,4-dinitrophenoxy)acetic acid. The preparation method of the invention has the advantages of simple process operation, short reaction time, no need for high temperature, high product purity and high yield, and the whole process is green and environmentally friendly, with less three wastes.
Description
technical field [0001] The invention relates to the field of preparation of pesticide raw materials, in particular to a preparation method of 2-(5-fluoro-2,4-dinitrophenoxy)acetic acid. Background technique [0002] 2-(5-Fluoro-2,4-dinitrophenoxy)acetic acid is an important pesticide intermediate used in the preparation of N-phenylphthalimide herbicide propargylfluramid. 2-(5-fluoro-2,4-dinitrophenoxy)acetic acid and its esters are hydrogenated under palladium / carbon or platinum / carbon catalysis to obtain 6-amino-7-fluoro-1,4-benzoxazine- 3(4H)-ketone (US4803270, Bioscience Biotechnology and Biochemistry, 1994, 58(4), 788-789), 6-amino-7-fluoro-4-propynyl-1,4-benzoxazine-3(4H )-ketone reacts with 3,4,5,6-tetrahydrophthalic anhydride to prepare flumecil propargyl (US5108488, US4640707). [0003] At present, the preparation methods of 2-(5-fluoro-2,4-dinitrophenoxy)acetic acid reported in the literature mainly include 3-fluorophenol method, 2,4-difluoronitrobenzene method an...
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