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Method for preparing organic fluorine compound

A compound and organic fluorine technology, applied in the field of preparation of organic fluorine compounds, can solve problems such as harsh reaction conditions and narrow substrate range, and achieve good yield, simple operation process, and mild reaction conditions

Active Publication Date: 2022-03-01
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have disadvantages such as the use of transition metal catalysts, relatively harsh reaction conditions, and narrow substrate ranges.

Method used

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  • Method for preparing organic fluorine compound
  • Method for preparing organic fluorine compound
  • Method for preparing organic fluorine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: Preparation of 4-nitrobenzylfluoride

[0026]

[0027] In a 100ml one-necked flask, add 4-nitrobenzyl alcohol (formula I, R=4-NO 2 )3.06g (20mmol), 1.16g (20mmol) potassium fluoride, 0.66g (6.5mmol) triethylamine and 40ml acetonitrile, in a sulfonyl fluoride atmosphere, stirred at 20°C for 8h, after the reaction, add 50ml water Dilute, then add 50ml of ethyl acetate to extract three times, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter with suction, and concentrate to obtain 2.84g of 4-nitrobenzylfluoride with a purity of 98%. Rate 90%.

[0028] Proton NMR spectrum: (500MHz, DMSO-d 6 )δ8.27(d, J=8.2Hz, 2H), 7.68(d, J=8.2Hz, 2H), 5.61(d, J=46.8Hz, 2H).

Embodiment 2

[0029] Embodiment 2: Preparation of 4-cyanobenzylfluoride

[0030]

[0031] In a 100ml single-necked flask, add 4-cyanobenzyl alcohol (formula I, R=4-CN) 3.06g (20mmol), 1.16g (20mmol) potassium fluoride, 6.08g (20mmol) 1,8- Diazabicyclo[5.4.0]undec-7-ene and 40ml of acetonitrile were stirred in a sulfonyl fluoride atmosphere at 60°C for 4h. After the reaction was completed, dilute with 50ml of water, and then add 50ml of ethyl acetate for extraction Combine the organic phases three times, wash with saturated brine, dry over anhydrous sodium sulfate, filter with suction, and concentrate to obtain 2.48 g of 4-cyanobenzylfluoride with a purity of 99% and a yield of 91%.

[0032] Proton NMR spectrum: (500MHz, Chloroform-d) δ7.84-7.62(m, 2H), 7.49(dt, J=7.8, 1.3Hz, 2H), 5.47(d, J=46.9Hz, 2H).

Embodiment 3

[0033] Embodiment 3: the preparation of 4-(fluoromethyl)-methyl benzoate

[0034]

[0035] In a 100ml one-necked flask, successively add 4-(hydroxymethyl) methyl benzoate (formula I, R=4-CO 2 Me) 3.32g (20 mmol), 1.16g (20mmol) potassium fluoride, 7.60g (50mmol) 1,8-diazabicyclo [5.4.0] undec-7-ene and 40ml dichloromethane, in In a sulfonyl fluoride atmosphere, stir at 70°C for 3 hours. After the reaction, add 50ml of water to dilute, then add 50ml of ethyl acetate to extract three times, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, and filter with suction. After concentration, 3.05 g of methyl 4-(fluoromethyl)-benzoate was obtained with a purity of 98% and a yield of 89%.

[0036] Proton NMR spectrum: (500MHz, DMSO-d 6 )δ8.01(d, J=7.7Hz, 2H), 7.55(d, J=7.8Hz, 2H), 5.54(d, J=47.1Hz, 2H), 3.87(s, 3H).

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Abstract

The invention discloses a method for preparing an organic fluorine compound, which comprises the following steps: mixing an alcohol compound (I), a fluorinating reagent, alkali and a solvent, reacting for 2-8 hours at 20-80 DEG C in a sulfonyl fluoride gas atmosphere, and then post-processing to obtain the organic fluorine compound (II), the method has the advantages of mild reaction conditions, no need of transition metal catalysis, use of cheap and easily available sulfonyl fluoride gas, efficient promotion of the preparation of the organic fluorine compound from alcohol and a fluorination reagent, wide substrate applicability, obtaining of the corresponding organic fluorine compound at a good yield, simple operation process, high efficiency, economy, and suitableness for large-scale preparation.

Description

technical field [0001] The invention relates to a method for preparing organic fluorine compounds, in particular to a novel method for preparing organic fluorine compounds by using sulfuryl fluoride gas to efficiently promote the reaction of alcohols and fluorinating reagents. Background technique [0002] Organofluorine compounds, due to the unique properties of fluorine element, highly charged fluorine compounds (OFCs) play an important role in pharmaceutical, agrochemical industry and materials chemistry, and have attracted extensive attention. [0003] The synthesis methods of organic fluorides reported in the literature mainly include: (1) nucleophilic reaction of halogenated hydrocarbons and basic fluorinating reagents to prepare organic fluorides; (2) decarboxylation and fluorination of carboxylic acids to prepare organic fluorides; Preparation of organic fluorides by free radical or metal catalyzed deoxyfluorination. However, these methods have disadvantages such as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B39/00C07C201/12C07C205/11C07C253/30C07C255/50C07C17/16C07C22/08C07C67/307C07C69/76C07C45/63C07C47/55C07C313/04
CPCC07B39/00C07C201/12C07C253/30C07C17/16C07C67/307C07C45/63C07C313/04C07C205/11C07C255/50C07C22/08C07C69/76C07C47/55
Inventor 张国富桑志旻王慧敏丁成荣吕井辉
Owner ZHEJIANG UNIV OF TECH