Preparation method for m-trifluoromethyl acetophenone and intermediate thereof

A technology of trifluoromethyl acetophenone and toluene solution, which is applied in the field of preparation of trifluoromethyl acetophenone and its intermediates, can solve the problems of many reaction steps, easy flushing, and low yield, and achieve the goal of reaction The effect of short time and high productivity

Inactive Publication Date: 2016-04-06
LIAONING TIANYU CHEM +4
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0026] The technical problem to be solved by the present invention is, in order to overcome the need to go through salt formation, diazo, coupling, hydrolysis when using m-trifluoromethylaniline as raw material to prepare m-trifluoromethyl acetophenone in the prior art, many reaction steps , the yield is not high, the amount of waste water is large, and when directly preparing the Grignard reagent with me...

Method used

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  • Preparation method for m-trifluoromethyl acetophenone and intermediate thereof
  • Preparation method for m-trifluoromethyl acetophenone and intermediate thereof
  • Preparation method for m-trifluoromethyl acetophenone and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1 Grignard

[0062] Using m-chlorotrifluorotoluene (I) as raw material

[0063] Add 212 mg of anhydrous lithium chloride to a 100 mL four-necked flask equipped with a magnetic stirrer, a thermometer, and a condenser, and replace nitrogen three times. Then 18.1 g (0.1 mol) of m-chlorobenzotrifluoride (I) was added, and at room temperature, 40.0 mL of 2.5 mol / L (0.1 mol) isopropylmagnesium chloride tetrahydrofuran solution was added dropwise, and the drop was completed in 30 minutes. Heat to reflux (70° C.) and keep warm for 3 hours until the area content of the raw material m-chlorobenzotrifluoride is less than 5% (GC detection). At this time, the area content of benzotrifluoride was 94.0%.

Embodiment 2

[0064] Embodiment 2 Grignard

[0065] Using m-chlorotrifluorotoluene (I) as raw material

[0066] In a 100mL four-neck flask equipped with a magnetic stirrer, a thermometer, and a condenser tube, nitrogen was injected three times, and then 18.1g (0.1mol) of m-chlorobenzotrifluorotoluene (I) was added, and 2.5mol / L (0.1 mol) of isopropylmagnesium chloride tetrahydrofuran solution 40.0mL, dripped in 30 minutes. Heat to reflux (70° C.) and keep warm for 3 hours until the area content of the raw material m-chlorobenzotrifluoride is less than 5% (GC detection). At this time, the area content of benzotrifluoride was 89.3%.

Embodiment 3

[0067] Embodiment 3 Grignard

[0068] Using m-bromobenzotrifluoride (II) as raw material

[0069] Add 212 mg of anhydrous lithium chloride to a 100 mL four-necked flask equipped with a magnetic stirrer, a thermometer, and a condenser, and replace nitrogen three times. Then 22.5 g of m-bromobenzotrifluoride (II) was added, and 40.0 mL of 2.5 mol / L isopropylmagnesium chloride tetrahydrofuran solution was added dropwise at room temperature, and the dropwise was completed in 30 minutes. Heating to 70° C. and insulated for 3 hours, detected by GC, the area content of m-chlorobenzotrifluoride is less than 5%, and the area content of benzotrifluoride is 97.2%. (IV).

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Abstract

The invention discloses a preparation method for m-trifluoromethyl acetophenone and an intermediate thereof. The preparation method comprises the steps of (a) Grignard reaction, wherein a compound A reacts with a Grignard reagent in a non-protonic solvent at the reaction temperature of 0-200 DEG C to obtain a compound B, the Grignard reagent is one or more of isopropylmagnesium chloride, isopropylmagnesium bromide, cyclohexylmagnesium chloride, cyclohexylmagnesium bromide, tert-butylmagnesium chloride and tert-butylmagnesium bromide, and the molar ratio of the Grignard reagent to the non-protonic solvent to the compound A is (0.9-2) to (2-20) to 1; (b) acetylization, wherein the compound B obtained in the step (a) reacts with an acetylization reagent in a non-protonic solvent at the reaction temperature between -40 DEG C and 200 DEG C to obtain the m-trifluoromethyl acetophenone. The reaction process is mild, and the preparation method is suitable for industrial mass production.

Description

Technical field [0001] The invention relates to a preparation method of trifluoromethylacetophenone and its intermediates. Background technique [0002] 3-Trifluoromethylacetophenone, or TFMAP for short, is an important intermediate in the synthesis of methoxyacrylate compound trifloxystrobin. It is also used in the fields of medicine, dyes, and liquid crystal materials. important raw materials. [0003] There are many synthesis methods for m-trifluoromethylacetophenone, the main ones are as follows: [0004] (1) Grignard reaction between m-trifluoromethylbenzonitrile and methyl iodide; [0005] [0006] Simons J. J Am Chem Soc., 1948, 70, 2837-2843. [0007] (2) Trifluoromethylbenzoic acid is acid chlorinated and then reacted with cadmium reagent of methyl iodide; [0008] [0009] Simons JH, Bond RL, McArthur RE. The preparation and properties of certain trifluoromethyl compounds [J]. J. Am. Chem. Soc., 1940, 62(12): 3477-3480. [0010] (3) Reaction of trifluoro...

Claims

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Application Information

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IPC IPC(8): C07C49/80C07C45/45C07F3/02
CPCC07C45/455C07F3/02C07C49/80
Inventor 樊小彬王海洋许可谢小震郑中博
Owner LIAONING TIANYU CHEM
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