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Aryl sulfur fluoride type fluorination reagent and preparation method thereof

A technology of aryl sulfur fluoride and radical sulfur fluoride, which is applied in the field of aryl sulfur fluoride type fluorinated reagents and its preparation, and can solve problems such as instability, low thermal decomposition temperature, and easy explosion

Active Publication Date: 2009-03-18
APELOA PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The biggest disadvantage of the above-mentioned dialkylamine sulfur fluoride fluoride reagents is that the product is liquid, the thermal decomposition temperature is low, the stability is poor, and it is prone to explosion during purification, especially at high temperature and violent vibration. It is extremely unstable and prone to explosion. explode
This brings great difficulties to the production and transportation of such fluorinated reagents

Method used

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  • Aryl sulfur fluoride type fluorination reagent and preparation method thereof
  • Aryl sulfur fluoride type fluorination reagent and preparation method thereof
  • Aryl sulfur fluoride type fluorination reagent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1 Preparation of 4-formic acid thiobenzene trifluoride (I-1a) and 4-ethoxycarbonyl thiobenzene trifluoride (I-1b)

[0049]

[0050] 1. Preparation of methyl 4-(dimethylaminothioformyloxy)benzoate (5)

[0051] Add 30g (0.197mol) methyl p-hydroxybenzoate to a 500mL single-necked bottle, dissolve it with 210mL N, N-dimethylformamide (DMF), and add 11.8g (0.295mmol) NaH ( 60%), stirred for 30 minutes. Add 48.7g (0.394mol) dimethylaminothioformyl chloride to the reactant, heat to 85°C and react until the reaction is complete (about 5 hours) monitored by TLC. Stop the reaction, cool the reaction liquid to room temperature, slowly pour it into water, stir for 30 minutes, filter, wash the filter cake with water three times, and dry to obtain 43.3 g of off-white solid (5), with a yield of 91.7%.

[0052] 1 H NMR (CDCl 3 ): δ3.36(s, 3H), 3.46(s, 3H), 3.91(s, 3H), 7.13(d, J=8.64Hz, 2H), 8.08(d, J=8.64Hz, 2H).

[0053] 2. Preparation of methyl 4-dimethylcarbamoylthi...

Embodiment 2～5

[0074] The mode of operation and process are carried out by the method of embodiment 1. The results are shown in Table 3.

[0075] Table 3 Examples 2-5

[0076]

Embodiment 6

[0077] The preparation of embodiment 6 4-cyanothiobenzene trifluoride (I-6)

[0078]

[0079] 1. Preparation of 4-(dimethylaminothioformyloxy)benzonitrile (10)

[0080] In a 1000mL single-necked flask equipped with magnetic stirring, spherical condenser and drying tube, add 30g (0.252mol) p-cyanophenol, add 300mL N, N-dimethylformamide (DMF) to dissolve, and cool in an ice-salt bath 15.1 g (0.378 mol) NaH (60%) was added in portions and stirred for 30 minutes. Add 62.2 g (0.503 mol) of dimethylthiocarbamoyl chloride to the reaction solution, heat to 85° C., and monitor by TLC until the reaction is complete. Heating was stopped, the reaction liquid was cooled to room temperature, slowly added to 1.2 L of water, stirred for 30 minutes, filtered, the filter cake was washed three times with water, and recrystallized from ethanol to obtain 41.5 g of off-white solid (10), yield 86.1%.

[0081] 1 H NMR (CDCl 3 ): δ 3.36 (s, 3H), 3.45 (s, 3H), 7.18 (d, J=8.52Hz, 2H), 7.70 (d, J...

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Abstract

The present invention discloses an aryl sulfur fluoride type fluoro reagent, and a method for preparing the same. The structure of the fluoro reagent is shown as formula (I), wherein R can be selected from carboxy group, carboxylate, substituted or unsubsitituted amic formacyl, nitrile group, sulfonic group, sulphonic acid ester group, single substituent of trifluoromethyl, or the same or different polysubstituting group. The fluoro reagent is large in molecular weight, solid, and suitable for production and transportation. The compound can be applied to the fluoro of various types of functional group, in particular to the double fluoro of ketone, and thus a safe and effective fluoro reagent is provided to the nucleophilic double fluoro reaction.

Description

technical field [0001] The invention relates to a novel structure of aryl sulfur fluoride type fluorinated reagents and a preparation method thereof. Background technique [0002] The fluorine atom (F) is the smallest atom among group VII elements and has the highest electronegativity among all elements. After introducing F or fluorine-containing groups into organic molecules, the electron cloud distribution of the entire molecule will shift, the dipole moment, acidity and alkalinity of the molecules will be affected, and the properties and molecular configurations of adjacent groups will also be affected. Changes will affect the physical and chemical properties of organic molecules. Therefore, introducing F into a specific position in an organic molecule can make it produce special properties and effects. A large number of fluorine-containing compounds have been synthesized and have been widely used in various fields such as pesticides, medicines, materials, atomic energy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C381/00C07B39/00
Inventor 杨勤胡键
Owner APELOA PHARM CO LTD
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