Novel process for preparing N-fluorobenzenesulfonimide with one-step method

A fluorobisbenzenesulfonimide, a new process technology, applied in the field of one-step preparation of N-fluorobisbenzenesulfonimide, can solve the problem of low reaction temperature, low yield, N-fluorobisphenyl Solve the problem of unsafe preparation reaction of sulfonimide, and achieve the effect of less side reactions and high yield

Active Publication Date: 2015-12-16
HUBEI ZHUOXI FLUOROCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The present invention is to solve the problems of unsafe preparation reaction of N-fluorobisbenzenesulfonimide, low reaction temperature and low yield

Method used

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  • Novel process for preparing N-fluorobenzenesulfonimide with one-step method
  • Novel process for preparing N-fluorobenzenesulfonimide with one-step method
  • Novel process for preparing N-fluorobenzenesulfonimide with one-step method

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Experimental program
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Embodiment 1-15

[0027] The synthesis of embodiment 1-15N-fluorinated bisbenzenesulfonylimide

[0028] First, fully stir the p-substituted bisbenzenesulfonimide, metal fluoride and perfluoroalkylsulfonyl fluoride with industrial acetonitrile; The gas is introduced from the final reaction tower; during the reaction process, the flow rate of the fluorine-nitrogen mixed gas is controlled to ensure that the reaction is carried out gently between -20 ° C and 60 ° C; after the reaction is completed, suction filtration, washing, and recrystallization are obtained. N-fluorobisbenzenesulfonimide.

[0029] Table 1 lists the data for the synthesis of N-fluorobisbenzenesulfonimide under different reaction conditions.

[0030] The list of experimental data of table 1 embodiment

[0031]

[0032]

[0033]

[0034] The above data show that:

[0035] 1: Whether to add perfluorobutylsulfonyl fluoride to the reaction system will significantly affect the yield of N-fluorobisbenzenesulfonimide. The o...

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Abstract

The invention provides a novel process for preparing N-fluorobenzenesulfonimide with a one-step method. A multistage tower reactor technological process is adopted, an acetonitrile solution of p-substituted dibenzenesulfonimide, metal fluoride and perfluoroalkyl sulfonyl fluoride and fluorine and nitrogen mixed gas enter a multistage reaction tower from two ends respectively, the concentration of p-substituted dibenzenesulfonimide and metal fluoride is reduced stage by stage from a first-stage reaction tower to a last-stage reaction tower, the concentration of fluorine gas is reduced stage by stage from the last-stage reaction tower to the first-stage reaction tower, and the acetonitrile solution of p-substituted dibenzenesulfonimide, metal fluoride and perfluoroalkyl sulfonyl fluoride and the fluorine and nitrogen mixed gas have a gas-liquid countercurrent reaction in the multistage reaction tower. In the process, the reaction temperature can be adjusted by controlling the fluorine introduction speed, and N-fluorobenzenesulfonimide is prepared with the one-step method at any temperature ranging from subzero 20 DEG C to 60 DEG C, the yield is higher than 90%, the reaction is safe and controllable, and few side reactions are caused. Perfluoroalkyl sulfonyl fluoride is taken as a wetting agent and can increase the reaction speed and the yield.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a new process for preparing N-fluorobisbenzenesulfonimide in one step. Background technique [0002] Electrophilic fluorinated reagents can electrophilicly substitute aromatic rings, carbonyl compounds, enol ethers, enol esters and other compounds to generate fluorine-containing compounds, which is a very important method for the synthesis of fluorine-containing compounds. These electrophilic fluorine reagents mainly include the following categories: (1) F 2 , XeF 2 ; (2) Reagents containing O-F bonds include CF 3 OF,CH 3 COOF, etc.; (3) Reagents containing X-F bonds, such as FClO 3 etc.; (4) Reagents containing N-F bonds, which are the largest class of electrophilic fluorinated reagents. N-F bond electrophilic fluorinated reagents, whose fluorination ability comes from the F connected to the electronegative N atom, because the electronegativity of the N atom is smaller tha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/48C07C303/40
Inventor 黄澄华李训生金广泉陈雪娟李菁吴荣
Owner HUBEI ZHUOXI FLUOROCHEM
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