CN102531962A - Preparation method of 2-fluorin-5-chlorobenzonitrile - Google Patents
Preparation method of 2-fluorin-5-chlorobenzonitrile Download PDFInfo
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- CN102531962A CN102531962A CN 201010618131 CN201010618131A CN102531962A CN 102531962 A CN102531962 A CN 102531962A CN 201010618131 CN201010618131 CN 201010618131 CN 201010618131 A CN201010618131 A CN 201010618131A CN 102531962 A CN102531962 A CN 102531962A
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- chlorobenzonitrile
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Abstract
The invention provides a preparation method of 2-fluorin-5-chlorobenzonitrile. In the method, 2,5-dichlorobenzonitrile and active potassium fluoride are taken as raw materials, sulfolane is taken as a solvent, and a phase transfer catalyst is added for reacting; sulfolane serving as the solvent is recyclable, so that production method is reduced; and the method is a synthesis method with a good prospect. Reaction operation is simple and practicable, and the method has industrial production application value.
Description
Technical field
The present invention relates to the fluorine chemical field, be specifically related to the compound method of 2-fluoro-5-6-chlorophenyl nitrile.
Background technology
Fluorine-containing heterocycles is mainly fluorine-containing pyridine series etc.; These midbodys are mainly used in synthetic pesticide, medicine and dyestuff etc.; The fast development of midbody has promoted the exploitation of the fluorine-containing fine chemicals in downstream, and at present the domestic fluorine-containing medicines of having developed and having produced, agricultural chemicals and dyestuff are nearly hundred kinds.From structure, commercial up to now fluorine-containing sterilant all is the compound of contain fluorine atoms on the phenyl ring.
Summary of the invention
The object of the present invention is to provide from the method for the initial catalysis Synthetic 2 of the reagent that is easy to obtain-fluoro-5-6-chlorophenyl nitrile.Have now found that a kind of preparation method of 2-fluoro-5-6-chlorophenyl nitrile, it is with 2, and 5-dichlorobenzonitrile and active Potassium monofluoride are raw material, make solvent with tetramethylene sulfone, react with phase-transfer catalyst.
Wherein, described catalyzer is quaternary ammonium salt, crown ether, polyethers etc., preferred quaternary ammonium salt.
Wherein, temperature of reaction is 170-240 degree centigrade.
Wherein, the reaction times is 4-7h.
Preferably, in the organic solvent that is selected from halogenated or not halogenated aliphatic series, alicyclic, aromatic hydrocarbon, carry out said reaction, the preferred hexane of said organic solvent, hexanaphthene, methylcyclohexane, toluene, mono chloro benzene, glycerine.
According to batch mode, optional solvent, reactant and catalyzer are infeeded in the reactor drum.Be heated to the temperature that preceding text limit.Apply desirable pressure and maintenance.When reaction finishes, according to the solid/liquid separation technique of routine, preferably via filtration, separating catalyst.Reclaim the product that is obtained by routine, preferably perhaps pass through liquid/liquid extraction through distillation.
Embodiment
Provide below and be used to illustrate and nonrestrictive exemplary of the present invention.
In an embodiment, transformation efficiency is corresponding to the ratio of the substrate mole number that transforms with the substrate mole number that infeeds, and given yield is corresponding to the ratio of the product mole number that forms with the substrate mole number that infeeds.
Embodiment 1
In having the 250mL four-hole boiling flask of whisking appliance, water trap, spherical condensation tube, TM, add tetramethylene sulfone 0.5mol, 2 respectively; 5-dichlorobenzonitrile 1.2mol and anhydrous potassium fluoride 15g; Add 10mL toluene, add 10 tetrabutylammonium chlorides again as catalyzer.Connect well heater, the water in the water trap is in time emitted in the temperature rising reflux dehydration.After the no globule is taken out of in the water trap, steam toluene, be warming up to 215～240 ℃ after adding the 10mL tetramethylene sulfone, insulation 6h.Get product 25.7g.
Embodiment 2
In having the 250mL four-hole boiling flask of whisking appliance, water trap, spherical condensation tube, TM, add tetramethylene sulfone 1.5mol, 2 respectively; 5-dichlorobenzonitrile 1.8mol and anhydrous potassium fluoride 19g; Add 10mL toluene, add 10 tetrabutylammonium chlorides again as catalyzer.Connect well heater, the water in the water trap is in time emitted in the temperature rising reflux dehydration.After the no globule is taken out of in the water trap, steam toluene, be warming up to 215～240 ℃ after adding the 15mL tetramethylene sulfone, insulation 6h.Get product 28.7g.
Embodiment 3
In having the 250mL four-hole boiling flask of whisking appliance, water trap, spherical condensation tube, TM, add tetramethylene sulfone 2.5mol, 2 respectively; 5-dichlorobenzonitrile 2.2mol and anhydrous potassium fluoride 25g; Add 20mL toluene, add 10 tetrabutylammonium chlorides again as catalyzer.Connect well heater, the water in the water trap is in time emitted in the temperature rising reflux dehydration.After the no globule is taken out of in the water trap, steam toluene, be warming up to 215～240 ℃ after adding the 16mL tetramethylene sulfone, insulation 6h.Get product 29.9g.
Claims (4)
1. the preparation method of a 2-fluoro-5-6-chlorophenyl nitrile, it is with 2, and 5-dichlorobenzonitrile and active Potassium monofluoride are raw material, make solvent with tetramethylene sulfone, react with phase-transfer catalyst.
2. the method for claim 1 is characterized in that, described catalyzer is quaternary ammonium salt, crown ether, polyethers etc., preferred quaternary ammonium salt.
3. the method for claim 1 is characterized in that, temperature of reaction is 170-240 degree centigrade.
4. the method for claim 1 is characterized in that, the reaction times is 4-7h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010618131 CN102531962A (en) | 2010-12-30 | 2010-12-30 | Preparation method of 2-fluorin-5-chlorobenzonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010618131 CN102531962A (en) | 2010-12-30 | 2010-12-30 | Preparation method of 2-fluorin-5-chlorobenzonitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102531962A true CN102531962A (en) | 2012-07-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201010618131 Pending CN102531962A (en) | 2010-12-30 | 2010-12-30 | Preparation method of 2-fluorin-5-chlorobenzonitrile |
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| CN (1) | CN102531962A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105899488A (en) * | 2013-11-12 | 2016-08-24 | 美国陶氏益农公司 | Process for fluorinating compounds |
| CN111454174A (en) * | 2019-01-18 | 2020-07-28 | 南通泰禾化工股份有限公司 | Method for preparing fluorobenzonitrile |
-
2010
- 2010-12-30 CN CN 201010618131 patent/CN102531962A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105899488A (en) * | 2013-11-12 | 2016-08-24 | 美国陶氏益农公司 | Process for fluorinating compounds |
| CN105899488B (en) * | 2013-11-12 | 2019-09-03 | 美国陶氏益农公司 | By the fluorinated method of compound |
| CN111454174A (en) * | 2019-01-18 | 2020-07-28 | 南通泰禾化工股份有限公司 | Method for preparing fluorobenzonitrile |
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| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
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Application publication date: 20120704 |