Synthesizing method for 4-oxethyl-1,1,1-trifluoro-butene-2-ketone

Abstract

The invention relates to a synthesizing method for 4-oxethyl-1,1,1-trifluoro-butene-2-ketone. The method comprises the following steps that dichloromethane and pyridine are added in a reaction kettle, on the condition that the temperature is controlled at minus 10 DEG C-0 DEG C, trifluoroacetic acid is dropwise added, the dropwise adding time is controlled for 3-3.5 hours, and after dropwise adding is completed, stirring is performed for ten minutes; vinyl ethyl ether is added, on the condition that the temperature is controlled at minus 10 DEG C-0 DEG C, methylsulfonyl chloride is dropwise added, the dropwise adding time is controlled for 2 hours, after dropwise adding is completed, the temperature is slowly increased to 20 DEG C, and stirring is performed for staying overnight; filter pressing is performed on obtained products with a plate-and-frame filter press, and filter cakes are washed for two times with dichloromethane to collect pyridinium; normal-pressure desolventizing is performed on filtrate at 58 DEG C, the temperature is lowered to 20 DEG C to collect solvent, reduced-pressure distilling and desolventizing are performed at 58 DEG C to collect solvent to obtain crude products, reduced-pressure rectifying is performed on the crude products to collect overhead products, and the 4-oxethyl-1,1,1-trifluoro-butene-2-ketone is obtained. The synthesizing method for the 4-oxethyl-1,1,1-trifluoro-butene-2-ketone has the advantages of being simple and direct in technology, few in technology waste materials, high in yield and suitable for large-scale industrialized production.

Description

technical field

[0001] The invention relates to a method for synthesizing a chemical intermediate, in particular to a method for synthesizing 4-ethoxy-1,1,1-trifluoro-buten-2-one. Background technique

[0002] Sulfoxaflor, whose chemical name is [1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-λ4-mercaptocyanamide, is a sulfoximide insecticide that acts on insects It acts on the unique binding site in the acetylcholine receptor to exert the insecticidal function, and can be absorbed by the roots and leaves into the plant.

[0003] 4-Ethoxy-1,1,1-trifluoro-buten-2-one is an important intermediate in the synthesis of sulfoxaflor, and 4-ethoxy-1,1,1-trifluoro- Most of buten-2-ones use trifluoroacetic anhydride as the starting material, and no direct synthesis of 4-ethoxy-1,1,1-trifluoro-buten-2-one with trifluoroacetic acid as raw material has been found. Related reports. Contents of the invention

[0004] The technical problem to be solved by the present invention is to provide...

Examples

Embodiment 1

[0010] Add 640kg of dichloromethane and 192kg of pyridine into the reaction kettle, add 136.8kg of trifluoroacetic acid dropwise under the condition of controlling the temperature at 0°C, and control the dropping time at 3.5 hours. Control the temperature at 0°C and add 145 kg of methanesulfonyl chloride dropwise for 2 hours. After the drop, slowly rise to 20°C and stir overnight; filter the obtained product with a plate and frame filter press, and the filter cake Wash twice with 50L of dichloromethane, collect the pyridinium salt, first precipitate the filtrate at 58°C under normal pressure, cool to 20°C, collect the solvent, then distill and precipitate under reduced pressure at 58°C, collect the solvent to obtain the crude product, and the crude product is passed through The distillate collected from the column at 48°C / 10mmHg was rectified under reduced pressure to obtain 182kg of 4-ethoxy-1,1,1-trifluoro-buten-2-one, with a yield of 90.3% and a chromatographic content of 99...

Embodiment 2

[0012] Add 640kg of dichloromethane and 192kg of pyridine into the reaction kettle, add 136.8kg of trifluoroacetic acid dropwise under the condition of controlling the temperature at -10°C, and control the dropping time at 3.5 hours. After the dropping is completed, stir for ten minutes, and then add 88kg of vinyl ether 145kg of methanesulfonyl chloride was added dropwise under the condition of controlling the temperature at -10°C, and the dropwise addition time was 2 hours. After the drop was completed, it was slowly raised to 20°C and stirred overnight; the obtained product was filtered with a plate and frame filter press, The filter cake was washed twice with 50L of dichloromethane, and the pyridinium salt was collected. The filtrate was precipitated at 58°C under normal pressure, cooled to 20°C, and the solvent was collected, then distilled under reduced pressure at 58°C, and the solvent was collected to obtain a crude product. The crude product was collected by distillatio...

Embodiment 3

[0014] Add 640kg of dichloromethane and 192kg of pyridine into the reaction kettle, and add 136.8kg of trifluoroacetic acid dropwise under the condition of controlling the temperature at -5°C. The dropping time is controlled at 3.5 hours. After the dropping is completed, stir for ten minutes, and add 88kg of vinyl ether 145kg of methanesulfonyl chloride was added dropwise under the condition of temperature control at -5°C, and the dropwise addition time was 2 hours. After the drop was completed, it was slowly raised to 20°C and stirred overnight; the obtained product was filtered with a plate and frame filter press, The filter cake was washed twice with 50L of dichloromethane, and the pyridinium salt was collected. The filtrate was precipitated at 58°C under normal pressure, cooled to 20°C, and the solvent was collected, then distilled under reduced pressure at 58°C, and the solvent was collected to obtain a crude product. The crude product was collected by distillation under r...

technical field

[0001] The invention relates to a method for synthesizing a chemical intermediate, in particular to a method for synthesizing 4-ethoxy-1,1,1-trifluoro-buten-2-one. Background technique

[0002] Sulfoxaflor, whose chemical name is [1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-λ4-mercaptocyanamide, is a sulfoximide insecticide that acts on insects It acts on the unique binding site in the acetylcholine receptor to exert the insecticidal function, and can be absorbed by the roots and leaves into the plant.

[0003] 4-Ethoxy-1,1,1-trifluoro-buten-2-one is an important intermediate in the synthesis of sulfoxaflor, and 4-ethoxy-1,1,1-trifluoro- Most of buten-2-ones use trifluoroacetic anhydride as the starting material, and no direct synthesis of 4-ethoxy-1,1,1-trifluoro-buten-2-one with trifluoroacetic acid as raw material has been found. Related reports. Contents of the invention

[0004] The technical problem to be solved by the present invention is to provide...

Examples

Embodiment 1

[0010] Add 640kg of dichloromethane and 192kg of pyridine into the reaction kettle, add 136.8kg of trifluoroacetic acid dropwise under the condition of controlling the temperature at 0°C, and control the dropping time at 3.5 hours. Control the temperature at 0°C and add 145 kg of methanesulfonyl chloride dropwise for 2 hours. After the drop, slowly rise to 20°C and stir overnight; filter the obtained product with a plate and frame filter press, and the filter cake Wash twice with 50L of dichloromethane, collect the pyridinium salt, first precipitate the filtrate at 58°C under normal pressure, cool to 20°C, collect the solvent, then distill and precipitate under reduced pressure at 58°C, collect the solvent to obtain the crude product, and the crude product is passed through The distillate collected from the column at 48°C / 10mmHg was rectified under reduced pressure to obtain 182kg of 4-ethoxy-1,1,1-trifluoro-buten-2-one, with a yield of 90.3% and a chromatographic content of 99...

Embodiment 2

[0012] Add 640kg of dichloromethane and 192kg of pyridine into the reaction kettle, add 136.8kg of trifluoroacetic acid dropwise under the condition of controlling the temperature at -10°C, and control the dropping time at 3.5 hours. After the dropping is completed, stir for ten minutes, and then add 88kg of vinyl ether 145kg of methanesulfonyl chloride was added dropwise under the condition of controlling the temperature at -10°C, and the dropwise addition time was 2 hours. After the drop was completed, it was slowly raised to 20°C and stirred overnight; the obtained product was filtered with a plate and frame filter press, The filter cake was washed twice with 50L of dichloromethane, and the pyridinium salt was collected. The filtrate was precipitated at 58°C under normal pressure, cooled to 20°C, and the solvent was collected, then distilled under reduced pressure at 58°C, and the solvent was collected to obtain a crude product. The crude product was collected by distillatio...

Embodiment 3

[0014] Add 640kg of dichloromethane and 192kg of pyridine into the reaction kettle, and add 136.8kg of trifluoroacetic acid dropwise under the condition of controlling the temperature at -5°C. The dropping time is controlled at 3.5 hours. After the dropping is completed, stir for ten minutes, and add 88kg of vinyl ether 145kg of methanesulfonyl chloride was added dropwise under the condition of temperature control at -5°C, and the dropwise addition time was 2 hours. After the drop was completed, it was slowly raised to 20°C and stirred overnight; the obtained product was filtered with a plate and frame filter press, The filter cake was washed twice with 50L of dichloromethane, and the pyridinium salt was collected. The filtrate was precipitated at 58°C under normal pressure, cooled to 20°C, and the solvent was collected, then distilled under reduced pressure at 58°C, and the solvent was collected to obtain a crude product. The crude product was collected by distillation under r...