Preparation method of haloxyfop-R-methyl

A high-efficiency technology of haloxyfop-pyl and trifluoromethylpyridine, which is applied in the direction of organic chemistry, can solve the problems of difficult preparation, complicated route, poor safety and environmental protection, etc., and achieves the advantages of industrial production, mild reaction conditions, and control The effect of production costs

Pending Publication Date: 2022-03-22
JIANGSU FLAG CHEM IND
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Problems solved by technology

The disadvantages of this method are: the use of chlorine is highly toxic and poor in safety and environmental protection; the high temperature and high pressure reaction requires too much equipment; the total yield of the three-step reaction is less than 80%, the route is complicated but the effect is not ideal, and it is not suitable for high-efficiency flupirin Industrialized Production of Methylhexapyl
Although the method achieves one-step preparation of the target product, its starting materials 2-fluoro-3-chloro-5-trif

Method used

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  • Preparation method of haloxyfop-R-methyl
  • Preparation method of haloxyfop-R-methyl
  • Preparation method of haloxyfop-R-methyl

Examples

Experimental program
Comparison scheme
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Example Embodiment

[0027] Example 1:

[0028]

[0029] (1) (R) -2- (4-hydroxyphenoxy) methyl propionate (formula II)

[0030] Benzene phenol (11g, 100 mmol), (R) -2-bromprolproprid (16.6 g, 100 mmol), potassium carbonate (20.7 g, 150 mmol), and DMF (110 ml) were added to 500 ml of three-necked. Reaction at 70 ° C for 8 h. The reaction liquid is cooled to room temperature, slowly add H. 2 O (200 mL), extracted twice with ethyl acetate (200 ml * 2), 20% NaCl aqueous solution was washed (100 mL), concentrated (R) -2- (4-hydroxyphenoxy) propionate 19.3g, The yield was 98.5%, HPLC purity 99.2%. ESI-MS (M / Z): 197.08 [M + H] + .

[0031] (2) (R) -2- (4 - ((3-chloro-5- (trifluoromethyl) pyridin-2-yl) oxygen) phenoxy) methyl propionate (formula I)

[0032] Add (R) -2- (4-hydroxyphenoxy) propionate (9.8 g, 50 mmol), 3-chloro-2-bromo-5-trifluoromethylpyridine (15.5 g). , 60 mmol), copper powder (160 mg, 2.5 mmO1) and DMF (100 mL), warmed to 80 ° C for 12 h. At the end of the reaction, the reaction liquid w...

Example Embodiment

[0033] Example 2:

[0034] (1) (R) -2- (4-hydroxyphenoxy) methyl propionate (formula II)

[0035] Benzene phenol (11g, 100 mmol), (R) -2-bromprolprolproprid (18.2 g, 110 mmol), potassium carbonate (20.7 g, 150 mmol) and DMF (110 ml), heating Reaction at 70 ° C for 8 h. The reaction liquid is cooled to room temperature, slowly add H. 2 O (200 mL), extracted twice with ethyl acetate (200 ml * 2), 20% NaCl aqueous solution was washed (100 mL), concentrated (R) -2- (4-hydroxyphenoxy) propionate 19g, The rate was 96.9%, HPLC purity 99.0%. ESI-MS (M / Z): 197.08 [M + H] + .

[0036] (2) (R) -2- (4 - ((3-chloro-5- (trifluoromethyl) pyridin-2-yl) oxygen) phenoxy) methyl propionate (formula I)

[0037] Add (R) -2- (4-hydroxyphenoxy) propionate (9.8 g, 50 mmol), 3-chloro-2-bromo-5-trifluoromethylpyridine (14.2 g). , 55 mmol), copper powder (160 mg, 2.5 mmO1) and DMF (100 mL), warmed to 80 ° C for 12 h. At the end of the reaction, the reaction liquid was cooled to room temperature, and 1% NH...

Example Embodiment

[0038] Example 3:

[0039] (1) (R) -2- (4-hydroxyphenoxy) methyl propionate (formula II)

[0040] Benzene phenol (11g, 100 mmol), (R) -2-bromprolproprid (16.6 g, 100 mmol), potassium carbonate (20.7 g, 150 mmol), and DMF (110 ml) were added to 500 ml of three-necked. Reaction at 60 ° C for 11h. The reaction liquid is cooled to room temperature, slowly add H. 2 O (200 mL), extract twice with ethyl acetate (200 ml * 2), 20% NaCl aqueous solution was washed (100 mL), concentrated (R) -2- (4-hydroxyphenoxy) propionate 18.8g, The yield was 95.9%, HPLC purity 99.0%. ESI-MS (M / Z): 197.08 [M + H] + .

[0041] (2) (R) -2- (4 - ((3-chloro-5- (trifluoromethyl) pyridin-2-yl) oxygen) phenoxy) methyl propionate (formula I)

[0042] Add (R) -2- (4-hydroxyphenoxy) propionate (9.8 g, 50 mmol), 3-chloro-2-bromo-5-trifluoromethylpyridine (15.5 g). , 60 mmol), copper oxide (198 mg, 2.5 mmO1) and DMF (100 mL), warmed to 80 ° C for 12 h. At the end of the reaction, the reaction liquid was cooled to r...

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Abstract

The invention discloses a preparation method of haloxyfop-R-methyl, which comprises the following steps: with hydroquinone as a raw material, reacting hydroquinone with (R)-2-methyl bromopropionate in the presence of an alkaline reagent to generate an intermediate (R)-2-(4-hydroxyphenoxy) methyl propionate; and then the haloxyfop-R-methyl and 3-chloro-2-bromo-5-trifluoromethylpyridine are directly prepared under the action of a catalyst to obtain the haloxyfop-R-methyl. The raw materials and reagents used in the method are cheap and easy to obtain, and the production cost can be effectively controlled; conditions are mild, operation is simple, and post-treatment is convenient; the prepared haloxyfop-R-methyl has high yield and purity, the optical purity of the target configuration (R) can reach 99%, the product quality is effectively guaranteed, and industrial production of the haloxyfop-R-methyl is better facilitated.

Description

technical field [0001] The invention belongs to the field of pesticide synthesis, and in particular relates to a preparation method of high-efficiency haloxyfop-pylene. Background technique [0002] High-efficiency fluroxyfop-pyl, the chemical name is 2-[4-(5-trifluoromethyl-3-chloro-pyridine-2-oxyl-)phenoxy]propionic acid methyl ester, is a new generation of fluorohetero High-efficiency herbicide. This species is a systemic conduction herbicide with good selectivity. It has excellent control effect on perennial stubborn grass weeds such as reed, imperata, and bermudagrass. It is highly safe for broad-leaved crops, and the effect is more stable under low temperature conditions. Compared with gazolone, high-efficiency haloxyfop-pyl replaces the ethoxyethyl group in gazolone with a methyl group in structure, and removes the inactive S configuration, which is a refined product of R configuration. At the same dose, it has higher and more stable activity than Gaygrass, and it i...

Claims

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Application Information

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IPC IPC(8): C07D213/643
CPCC07D213/643
Inventor 王正旭张璞吴耀军
Owner JIANGSU FLAG CHEM IND
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