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Preparation method of 1-[3-chloro-5-(trifluoromethyl) phenyl]-2, 2, 2-trifluoroethanone and derivatives thereof

A technology of trifluoromethylphenyl and trifluoromethyl, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of high price, difficulty and high production cost of trifluorotoluene, achieve good application prospects, cheap raw materials, and mild reaction conditions Effect

Active Publication Date: 2021-05-11
TAIZHOU ABSOBIOTEC CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the above technical solution, the price of 1-bromo-3-chloro-5-trifluorotoluene is relatively high, it is not easy, and the reaction needs to be carried out at -80°C, which leads to higher production costs for enterprises when expanding production

Method used

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  • Preparation method of 1-[3-chloro-5-(trifluoromethyl) phenyl]-2, 2, 2-trifluoroethanone and derivatives thereof
  • Preparation method of 1-[3-chloro-5-(trifluoromethyl) phenyl]-2, 2, 2-trifluoroethanone and derivatives thereof
  • Preparation method of 1-[3-chloro-5-(trifluoromethyl) phenyl]-2, 2, 2-trifluoroethanone and derivatives thereof

Examples

Experimental program
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Effect test

preparation example 1

[0050] Preparation Example 1: the preparation process of compound II.

[0051] Compound II is synthesized through Reaction Formula A.

[0052]

[0053]

[0054] Specifically include the following steps.

[0055] S1-1. Take 1.5mol (245.1g) of compound IV, dissolve it in a mixed solution formed by 1.5L diethyl ether solution and 1L 40% aqueous sodium hydroxide solution, and lower the temperature to 0°C, and then add 1.65mol tert-butylmethylmethanol uniformly within 0.5h Acyl chloride (198g) During the above process, the temperature was controlled below 5°C, then the temperature was raised to 20°C and the reaction was continued with stirring for 2.5h. After the reaction was completed, the temperature was lowered to 0° C. and stood still for 1.5 h, then filtered, and the filter residue was retained, washed twice with a mixed solution of water and methanol at a volume ratio of 9:1, and compound V was obtained after drying.

[0056] S1-2. Take 1mol (245g) of compound V, diss...

Embodiment 1

[0059] Example 1: The preparation method of 1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone is as follows.

[0060] S1. Compound II was synthesized according to Step S1-1, Step S1-2, and Step S1-3 in Preparation Example 1.

[0061] S2. Take 0.3 mol of the compound II synthesized in step S1, dissolve it in 300 mL of toluene (solvent I), prepare a 1M solution, heat it to 50 ° C, and add sulfuryl chloride (50.0 g, 0.37mol) as a chlorination reagent, added dropwise and stirred for 8 hours, then lowered to 25°C, added 400mL of water for rinsing, retained the organic phase, and obtained a solution containing compound III. It was determined that 84.3 g of compound III could be obtained after evaporating the solution to dryness, with a content of 99.4% and a yield of 96.4%.

[0062] S3. Cool the above-mentioned solution containing Compound III (containing 84.3 g of Compound III, 0.289 mol) to -10 to 0° C., and dropwise add 120 g of sulfuric acid with a mass fraction of...

Embodiment 2

[0063] Example 2: The preparation method of 1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone, the difference from Example 1 is as follows.

[0064] In step S2, the dissolved concentration of compound I in toluene is 0.5M, and after the system fully reacts with sulfonyl chloride, the temperature is lowered to 20°C.

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Abstract

The invention relates to the field of synthesis of drug intermediates, in particular to a preparation method of 1-[3-chloro-5-(trifluoromethyl) phenyl]-2, 2, 2-trifluoroethanone and derivatives thereof, and the method comprises the following steps: synthesizing a compound II by p-trifluoromethylaniline, then synthesizing a compound III by chlorination, and finally synthesizing the 1-[3-chloro-5-(trifluoromethyl) phenyl]-2, 2, 2-trifluoroethanone and derivatives thereof by diazotization deamination. In the whole reaction, conditions are mild, raw materials are easy to obtain, economic effects of enterprises can be improved, production cost is reduced, and the method is suitable for large-scale production.

Description

technical field [0001] This application relates to the field of synthesis of pharmaceutical intermediates, more specifically, it relates to the synthesis of 1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone and its derivatives Preparation. Background technique [0002] 1-[3-Chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone is used in the preparation of a new generation of oral anthelmintic drug AFOXOLANER for dogs important intermediates. On the basis of 1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone, the common ortho-position of its chlorine and trifluoroacetyl can be substituted It is further used to synthesize derivatives of various drugs, which is of great significance in drug research and development. [0003] The patent US2011105532 of German Bayer company provides a kind of synthetic method of 1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone, with 1-bromo- 3-Chloro-5-trifluorotoluene is used as the starting materi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/65C07C49/80C07C45/63C07C45/64C07C49/825
CPCC07C45/65C07C45/63C07C45/64C07C221/00C07C49/80C07C49/825C07C225/22
Inventor 张凌霄蔡刚华
Owner TAIZHOU ABSOBIOTEC CO LTD
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