Preparation method for 2-substituted 6-(trifluoromethyl)benzenesulphonyl chloride
A technology of trifluoromethylbenzenesulfonyl chloride and trifluorotoluene, which is applied in the field of preparation of 2-substituent-6-trifluoromethylbenzenesulfonyl chloride, can solve the problems of low reaction yield, low reaction yield and price Expensive and other issues, to achieve the effect of optimizing the synthesis process, simplifying the synthesis steps, and reducing production costs
Inactive Publication Date: 2015-02-11
TIANJIN NUOWEIKANG BIOTECH
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Problems solved by technology
6-trifluoromethyl-2-fluoroaniline is expensive and the degree of marketization is not high, and the reaction yield is low, and the operation is complicated, so this method causes certain difficulties for the synthesis of sulcolam
Its key intermediate 2-fluoro-6-trifluoromethylbenzenesulfonyl chloride can also be prepared from 2-bromo-3-fluorobenzotrifluoride (Bioorganic and Medicinal Chemistry, 2008, 16(3), 1345-1358), but the same Facing the problems of high price of 2-bromo-3-fluorobenzotrifluoride, low marketability and low reaction yield
Method used
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Embodiment 1
[0025] Preparation of 2-fluoro-6-trifluoromethylbenzenesulfonyl chloride
[0026]
[0027] Under nitrogen protection, 164.10 g (1.00 mol) of m-fluorobenzotrifluoride was dissolved in 3000 mL of anhydrous tetrahydrofuran and placed in a 10000 mL four-neck flask. -80°C, under electromagnetic stirring, slowly add 440 mL (1.10 mol) of 2.5 mol / L tert-butyllithium n-hexane solution into the four-neck flask dropwise. After the dropwise addition is completed, keep warm at -80°C for 1h.
[0028] Under the protection of nitrogen, 202.50 g (0.15 mol) of sulfuryl chloride was slowly added dropwise to the above-mentioned reaction solution of fluorobenzotrifluoride and tert-butyllithium. The dropping process was kept below -80°C and kept warm for 2h. The reaction solution was gradually raised to room temperature. Add 100 mL of saturated saline and stir for 5 min with magnetic force. After standing for separation, the organic layer was washed with saturated aqueous sodium bicarbonate,...
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A disclosed preparation method for 2-substituted 6-(trifluoromethyl)benzenesulphonyl chloride comprises preparation of 2-fluoro-6-(trifluoromethyl)benzenesulphonyl chloride. Concretely, the preparation method comprises: step 1, under protection of an inert gas, cooling an anhydrous solution of 3-substituted benzotrifluoride to -100 DEG C to -20 DEG C, and slowly adding a strong alkali into the solution; step 2, keeping warm for a period, dropwise adding sulfuryl chloride into the solution obtained in the step 1, and keeping a low temperature during dropwise adding; and step 3, performing washing, drying and desolventizing on the reaction solution obtained in the step 2, and directly performing a next-step reaction. A reaction general formula is shown in the specification.
Description
technical field [0001] The invention relates to a method for preparing 2-substituent-6-trifluoromethylbenzenesulfonyl chloride. Background technique [0002] 1-(2,2-Difluoroethoxy)-6-trifluoromethyl-N-(5,8-dimethoxy[1,2,4]triazol[1,5-C]pyrimidine -2-) Benzenesulfonamide, its chemical structure is as follows: [0003] [0004] 1-(2,2-Difluoroethoxy)-6-trifluoromethyl-N-(5,8-dimethoxy[1,2,4]triazol[1,5-C]pyrimidine -2-) Benzenesulfonamide is a post-emergence herbicide developed by DowAgro-Sciences, which works by inhibiting acetolactate synthase (ALS). Absorbed by stems, leaves, buds and roots, it is transmitted to the meristematic tissue through xylem and phloem, inhibits plant growth, causes growth points to lose chlorosis, necrosis, and then kills the entire plant. It is the variety with the widest herbicidal spectrum among the herbicides used in paddy fields. [0005] DowAgro-Sciences disclosed 1-(2,2-difluoroethoxy)-6-trifluoromethyl-N-(5,8-dimethoxy) in 1999 US pa...
Claims
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Login to View More IPC IPC(8): C07C309/86C07C303/10
Inventor 牛津梁
Owner TIANJIN NUOWEIKANG BIOTECH