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Preparation method of oriented single alkylation of 4-fluorine-N-isopropyl aniline

A technology for isopropylaniline and fluoroaniline, which is applied in the field of alkylation preparation of 4-fluoro-N-isopropylaniline, can solve the problems of complex reaction operation, difficult amplification, poor product quality and the like, and achieves conversion of raw materials The effect of high rate and high product quality

Active Publication Date: 2014-08-13
SINOCHEM LANTIAN +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] (1) The existing substituted alkylation reaction prepares the 4-fluoro-N-isopropylaniline method, the reaction selectivity is poor, the product yield is low, the product purification is difficult, and the product quality obtained is poor
[0011] (2) In the condensation-reduction alkylation reaction using 4-fluoronitrobenzene, acetone and hydrogen as raw materials, the reaction pressure is relatively high, and the products generated are complicated. The catalysts used are palladium or platinum series noble metal catalysts, which are easy to carry out in the reaction. Dehalogenation side reaction, it is easy to cause catalyst poisoning to cause catalyst failure
[0012] (3) In the method for preparing 4-fluoro-N-isopropylaniline by electrophilic amination reaction, the reaction operation is complex, the reaction conditions are harsh, and the reaction yield is low, only 45%
The reaction conditions are only suitable for laboratory research, such as industrial amplification, the amplification is very difficult

Method used

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  • Preparation method of oriented single alkylation of 4-fluorine-N-isopropyl aniline
  • Preparation method of oriented single alkylation of 4-fluorine-N-isopropyl aniline
  • Preparation method of oriented single alkylation of 4-fluorine-N-isopropyl aniline

Examples

Experimental program
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Effect test

Embodiment 1

[0040] In a 250ml three-necked reaction flask, connect a mechanical stirrer, a condenser tube and a dropping funnel. 22g of 4-fluoroaniline, 25g of isopropyl bromide, 0.5g of PEG-400, 0.2g of tetrabutylammonium bromide, 0.2g of dodecyltrimethylammonium chloride and 0.1g of iodine were added in one portion. Dissolve 8g of sodium hydroxide in 30g of water, prepare the sodium hydroxide solution and set aside. The temperature of the system was raised to 60° C. for reflux reaction, and the reflux reaction was performed for 6 hours under the condition that the stirring speed was 200 r / min. After the reaction was cooled down to room temperature, sodium hydroxide solution was added dropwise for 30 minutes, and after the dropwise addition was completed, the reaction was terminated after being kept warm for 30 minutes. For liquid separation, add 20 ml of 0.5 mol / L dilute hydrochloric acid solution to the organic phase, stir for 30 min, and then separate the liquid to take 30 g of the o...

Embodiment 2

[0042] In a 250ml three-necked reaction flask, connect a mechanical stirrer, a condenser tube and a dropping funnel. Add 24g of 4-fluoroaniline, 34g of isopropyl iodide, 0.3g of PEG-400, 0.3g of tetrabutylammonium bromide, and 0.2g of tetramethylammonium chloride at one time. Dissolve 7g of sodium hydroxide in 30g of water, prepare the sodium hydroxide solution and set aside. The temperature of the system was raised to 90° C. for reflux reaction, and the reflux reaction was performed for 4 hours under the condition that the stirring speed was 200 r / min. After the reaction was lowered to 30°C, sodium hydroxide solution was added dropwise for 30 minutes, and the reaction was terminated after the dropwise addition was completed and kept warm for 30 minutes. For liquid separation, add 20 ml of 0.5 mol / L dilute hydrochloric acid solution to the organic phase, stir for 30 min, and then separate the liquids to obtain 31 g of the organic phase. The organic phase liquid was analyzed ...

Embodiment 3

[0044] In a 250ml three-necked reaction flask, connect a mechanical stirrer, a condenser tube and a dropping funnel. 22g of 4-fluoroaniline, 15g of isopropyl chloride, 0.2g of PEG-400, 0.2g of tetrabutylammonium chloride, 0.2g of tetramethylammonium chloride and 0.5g of potassium iodide were added in one go. Dissolve 16g of potassium hydroxide (content is 85%) in 55g of water, configure potassium hydroxide solution, set aside. The temperature of the system was raised to 35° C. for reflux reaction, and the reflux reaction was performed for 8 hours under the condition that the stirring speed was 200 r / min. After the reaction was cooled down to room temperature, potassium hydroxide solution was added dropwise for 60 minutes, and after the dropwise addition was completed, the reaction was terminated after being incubated for 40 minutes. For liquid separation, add 20 ml of 0.5 mol / L dilute hydrochloric acid solution to the organic phase, stir for 30 min, and then separate the liqu...

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Abstract

The invention discloses a preparation method of 4-fluorine-N-isopropyl aniline by oriented single substituted N-alkylation reaction, which takes 4-fluoroaniline as a substrate, halogenated iso-propane as an alkylation reagent under the effects of a phase-transfer catalyst, a cocatalyst and an acid binding agent. The method has the advantages of mild reaction condition, simple operation, high raw material conversion rate and products selectivity, convenient products separation and the like. The prepared 4-fluorine-N-isopropyl aniline is an important pesticide intermediate, and can synthesize an oxyacetamide herbicide flufenacet and the like.

Description

technical field [0001] The invention relates to an alkylation preparation method of 4-fluoro-N-isopropylaniline. Background technique [0002] 4-Fluoro-N-isopropylaniline, the English name is 4-Fluoro-N-Isopropylanline, the molecular formula is C 9 h 12 FN, molecular weight 153, CAS number 70441-63-3. 4-Fluoro-N-isopropylaniline is an important pesticide intermediate from which the oxyacetamide herbicide flufenacet can be synthesized. The molecular structure of 4-fluoro-N-isopropylaniline can be regarded as a derivative in which the hydrogen in the ammonia molecule is replaced by isopropyl and fluorobenzene. Similar to inorganic ammonia, where the N atom is sp 3 Hybridization, there is a lone pair of electrons on the N atom, which reflects a series of chemical properties, such as the hydrogen on the amino group is prone to neutralization, acylation, sulfonation and other reactions, and a series of useful compounds can be synthesized. Its structural formula is as follows:...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/52C07C209/10
Inventor 李华徐卫国杨箭杨汪松蒋强
Owner SINOCHEM LANTIAN
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