CN102267871A - Preparation method of 3-chloro-4-fluorobenzotrifluoride - Google Patents
Preparation method of 3-chloro-4-fluorobenzotrifluoride Download PDFInfo
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- CN102267871A CN102267871A CN2010101983331A CN201010198333A CN102267871A CN 102267871 A CN102267871 A CN 102267871A CN 2010101983331 A CN2010101983331 A CN 2010101983331A CN 201010198333 A CN201010198333 A CN 201010198333A CN 102267871 A CN102267871 A CN 102267871A
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Abstract
The invention provides a preparation method of 3-chloro-4-fluorobenzotrifluoride. The method is characterized in the following steps that: under the existence of a catalyst, 3,4-dichlorotrifluorotoluene and anhydrous potassium fluoride are subject to a fluoridation reaction in a polar aprotic solvent. The catalyst contains copper halide and crown ether. According to the invention, 3,4-dichlorotrifluorotoluene and anhydrous potassium fluoride are subject to a fluoridation reaction in the polar aprotic solvent under the existence of the catalyst containing copper halide and crown ether. Therefore, a target product selectivity of 3-chloro-4-fluorobenzotrifluoride preparation is substantially improved, and the product purity is higher than 97%. With the preparation method, the reaction conditions are mild. The method is easy to be applied in industrialized productions.
Description
Technical field
The present invention relates to a kind of preparation method of 3-chloro-4-fluoride trifluoro toluene.
Background technology
3-chloro-4-fluoride trifluoro toluene is very important medicine and pesticide intermediate, and chemical structural formula is:
Molecular weight is 198.55.
According to existing bibliographical information, the preparation method of 3-chloro-4-fluoride trifluoro toluene mainly contains following several.
For example, disclose a kind of preparation method of 3-chloro-4-fluoride trifluoro toluene in the U.S. Pat 4582948, it is a raw material with 4-fluoro-3-nitro-trifluoromethyl toluene, prepares with chlorine reaction under 320-380 ℃ high temperature.This method need at high temperature be carried out chlorination, and is bigger in industrial difficulty.
For another example, a kind of preparation method of 3-chloro-4-fluoride trifluoro toluene is disclosed among the Japanese Patent JP59139329A, it is by 3,4-two chlorobenzotrifluorides and Potassium monofluoride react in the solvent of methyl-sulphoxide and/or dimethyl sulfone and under the oil bath condition and prepare, though this method uses 3,4-two chlorobenzotrifluorides are raw material, react with Potassium monofluoride, but among this preparation method, the reaction preference of 3-chloro-4-fluoride trifluoro toluene is low, a large amount of easily isomer 4-chloro-3-fluoride trifluoro toluenes that generate 3-chloro-4-fluoride trifluoro toluene.
Therefore, there is the preparation condition harshness in existing 3-chloro-4-fluoride trifluoro toluene preparation method, and selectivity of product is low, the shortcoming that products obtained therefrom purity is lower.
Summary of the invention
The objective of the invention is in order to solve in the prior art the low problem of selectivity of product in the 3-chloro-4-fluoride trifluoro toluene preparation process, provide a kind of selectivity of product the high and high 3-chloro-4-fluoride trifluoro toluene preparation method of product purity.
The present inventor is through discovering repeatedly, in the presence of the catalyzer of halogenide that contains copper and crown ether, with 3,4-two chlorobenzotrifluorides are raw material, can make 3-chloro-4-fluoride trifluoro toluene at an easy rate with the anhydrous potassium fluoride reaction in aprotic solvent.
Based on above-mentioned cognition, the invention provides a kind of preparation method of 3-chloro-4-fluoride trifluoro toluene, wherein, this preparation method is included under the existence of catalyzer, make 3,4-two chlorobenzotrifluorides and anhydrous potassium fluoride carry out fluoridation in polar aprotic solvent, described catalyzer contains the halogenide and the crown ether of copper.
Preparation method according to 3-chloro-4-fluoride trifluoro toluene of the present invention, by using 3,4-two chlorobenzotrifluorides and anhydrous potassium fluoride react in the presence of the catalyzer of halogenide that contains copper and crown ether, when making preparation 3-chloro-4-fluoride trifluoro toluene, target product selectivity significantly improves, prepared product purity is up to more than 97%, and this preparation method's reaction conditions gentleness, is easy to industrialization.
Embodiment
The preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention is included under the existence of catalyzer, makes 3, and 4-two chlorobenzotrifluorides and anhydrous potassium fluoride carry out fluoridation in polar aprotic solvent, and described catalyzer contains the halogenide and the crown ether of copper.Fluorination reaction process can be represented with following general formula:
As 3 of reaction initial feed, 4-two chlorobenzotrifluorides obtain easily industrial, can be with 3, and the 4-trichloro toluene dichloride is that raw material prepares by fluorination method, also can be commercially available, such as 3 of lark prestige Science and Technology Ltd., 4-two chlorobenzotrifluorides etc.
Potassium monofluoride obtains industrial easily as a kind of fluorizating agent commonly used, is anhydrous system in order to guarantee reaction system, in the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention, uses anhydrous potassium fluoride as fluorizating agent.
The preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention is significantly improved the selectivity of target product 3-chloro-4-fluoride trifluoro toluene by carry out fluoridation in the presence of the catalyzer of halogenide that contains copper and crown ether.In the preferred case, with described 3, the weight of 4-two chlorobenzotrifluorides is benchmark, and described catalyst consumption can be 0.1-3 weight %, is preferably 0.2-1 weight %.
Preparation method according to 3-chloro-4-fluoride trifluoro toluene of the present invention, as long as can realize purpose of the present invention though contain the halogenide and the crown ether of copper in the catalyzer, in the preferred case, in catalyzer, the halogenide of copper and the weight ratio of crown ether are 1-10: 1, and 2-5 more preferably: 1.The halogenide of the copper in the catalyzer and crown ether are in above-mentioned scope the time, can improve the selection rate of 3-chloro-4-fluoride trifluoro toluene, and then improve the purity of product 3-chloro-4-fluoride trifluoro toluene, and can guarantee further that fluoridation carries out under relatively mild reaction conditions, and the reaction conversion ratio height.
According to the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention, the halogenide of the copper in the catalyzer can be the halogenide of various copper, and for example cupric chloride, cuprous chloride, cupric bromide and bromize alpha ketone etc. are preferably cuprous chloride.
Preparation method according to 3-chloro-4-fluoride trifluoro toluene of the present invention, the crown ether that uses in the catalyzer can be various big cyclic ethers as phase-transfer catalyst, for example can be selected from 15-hat-5,18-hat-6 and bicyclohexane also-at least a in the 18-hat-6, be preferably 18-hat-6.These crown ethers can for example use alkoxide (being generally glycerine) and haloalkane to prepare by Williamson synthesis by preparing, and also can obtain by being purchased.
In order to obtain the selectivity and the fluoridation rate of best 3-chloro-4-fluoride trifluoro toluene, the preferred in the present invention catalyzer that contains cuprous chloride and 18-hat-6 that uses.
Preparation method according to 3-chloro-4-fluoride trifluoro toluene of the present invention, for reaction solvent, as long as can guarantee 3, the fluoridation of 4-two chlorobenzotrifluorides and anhydrous potassium fluoride is carried out smoothly, just there is no particular limitation, can use this area various polar aprotic solvents commonly used, be preferably and be selected from least a in dimethyl sulfoxide (DMSO), tetramethylene sulfone, N-Methyl pyrrolidone and the N,N-dimethylacetamide.For the consumption of reaction solvent, in order to guarantee 3,4-two chlorobenzotrifluorides fully contact in solvent with anhydrous potassium fluoride, further promote reactivity, in the preferred case, polar aprotic solvent and raw material 3, the weight ratio of 4-two chlorobenzotrifluorides can be 1-5: 1, be preferably 2-4: 1.
According to the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention, in the preferred case, the fluoridation of 3-chloro-4-fluoride trifluoro toluene and anhydrous potassium fluoride can be carried out under inert atmosphere.Described inert atmosphere only otherwise described fluoridation is caused negative impact, just there is no particular limitation, can be preferably nitrogen atmosphere for for example being selected from least a atmosphere in nitrogen, helium, neon, argon gas and the radon gas.
According to the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention, in order further to improve the reactivity of fluoridation, in the preferred case, and 3, the mol ratio of 4-two chlorobenzotrifluorides and described anhydrous potassium fluoride can be 1: 2-10 is preferably 1: 3-8; Temperature of reaction can be 150-230 ℃, is preferably 160-220 ℃; Reaction times can be 1-30 hour, is preferably 5-25 hour.
According to the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention, in the preferred case, after fluoridation, carry out rectification under vacuum, from reaction mixture, separate obtaining target product 3-chloro-4-fluoride trifluoro toluene.In the present invention, for the rectifying tower that is used for rectification under vacuum, can use this area various rectifying tower commonly used.For reduced pressure and cut temperature range, can suitably select according to the boiling point of 3-chloro-4-fluoride trifluoro toluene under the specific reduced pressure.Isolate 3-chloro-4-fluoride trifluoro toluene by rectification under vacuum, by removing by filter inorganic salt, especially the Repone K that the Potassium monofluoride of excessive use and reaction generate in the reaction under reduced pressure, reclaims solvent then with the mother liquor after the rectification under vacuum.
Embodiment
The present invention will be described in more detail with Comparative Examples by the following examples, but the present invention is not limited to following embodiment.
Embodiment 1
Present embodiment is used to illustrate the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention.
In 500 milliliters of four-hole boiling flasks with agitator, thermometer, pressure warning unit and rectifying column, add exsiccant dimethyl sulfoxide (DMSO) 200 grams, anhydrous potassium fluoride 53.3 gram (content 98%, 0.9mol), the cuprous chloride of 0.3 gram and the 18-hat-6 of 0.1 gram, add the back and feed nitrogen, make and remain nitrogen atmosphere in the flask, under agitation add 3 then, 4-two chlorobenzotrifluorides 65.2 gram (content 99%, 0.3mol), use heating of electrically heated cover and insulation at 170-180 ℃, reacted 20 hours.Under the decompression of 2000-1000Pa, 58-60 ℃ cut is collected in rectifying, gets product 49.3 grams, and by gas chromatographic analysis, 3-chloro-4-fluoride trifluoro toluene content is 99% in the product, and yield is 80%.Mother liquor after the rectification under vacuum is filtered, remove the salt of distillation mother liquor, under the decompression decompression of 2000-1500Pa, reclaim dimethyl sulfoxide (DMSO) then.
Comparative Examples 1
Except not having cuprous chloride and 18-hat-6, prepare 3-chloro-4-fluoride trifluoro toluene according to the method for embodiment 1, its as a result products obtained therefrom be 40.0 grams, by gas chromatographic analysis, 3-chloro-4-fluoride trifluoro toluene content is 92% in the product, yield is 65%.
Comparative Examples 2
Except the 18-hat-6 that uses 0.4g replaces the 18-hat-6 of 0.3 cuprous chloride that restrains and 0.1 gram as the catalyzer, method according to embodiment 1 prepares 3-chloro-4-fluoride trifluoro toluene, its as a result products obtained therefrom be 43.1 the gram, by gas chromatographic analysis, 3-chloro-4-fluoride trifluoro toluene content is 93% in the product, and yield is 70%.
Comparative Examples 3
Except replacing the cuprous chloride of 0.3 gram and the 18-of 0.1 gram, the cuprous chloride that uses 0.4g is preced with-6 as the catalyzer, method according to embodiment 1 prepares 3-chloro-4-fluoride trifluoro toluene, its as a result products obtained therefrom be 44.4 the gram, by gas chromatographic analysis, 3-chloro-4-fluoride trifluoro toluene content is 94% in the product, and yield is 72%.
Comparative Examples 4
Except the copper powder that uses 0.3g replaces the cuprous chloride of 0.3 gram, method according to embodiment 1 prepares 3-chloro-4-fluoride trifluoro toluene, its as a result products obtained therefrom be 42.5 the gram, by gas chromatographic analysis, 3-chloro-4-fluoride trifluoro toluene content is 90% in the product, and yield is 69%.
Embodiment 2
Present embodiment is used to illustrate the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention.
In 500 milliliters of four-hole boiling flasks with agitator, thermometer, pressure warning unit and rectifying column, add exsiccant N-Methyl pyrrolidone 261 grams, anhydrous potassium fluoride 142.1 gram (content 98%, 2.4mol), the cuprous chloride of 0.1 gram and the 18-hat-6 of 0.03 gram, add the back and feed nitrogen, make and remain nitrogen atmosphere in the flask, under agitation add 3 then, 4-two chlorobenzotrifluorides 65.2 gram (content 99%, 0.3mol), be suitable for heating of electrically heated cover and insulation at 160-170 ℃, reacted 25 hours.Under the decompression of 2000-1000Pa, 58-60 ℃ cut is collected in rectifying, gets product 48.1 grams, and by gas chromatographic analysis, 3-chloro-4-fluoride trifluoro toluene content is 98% in the product, and yield is 78%.Mother liquor after the rectification under vacuum is filtered, remove the salt of distillation mother liquor, under the decompression decompression of 2000-1500Pa, reclaim tetramethylene sulfone then.
Embodiment 3
Present embodiment is used to illustrate the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention.
In 500 milliliters of four-hole boiling flasks with agitator, thermometer, pressure warning unit and rectifying column, add exsiccant tetramethylene sulfone 130.4 grams, anhydrous potassium fluoride 53.3 gram (content 98%, 0.9mol), the cuprous chloride of 0.5 gram and the 18-hat-6 of 0.1 gram, add the back and feed nitrogen, make and remain nitrogen atmosphere in the flask, under agitation add 3 then, 4-two chlorobenzotrifluorides 65.2 gram (content 99%, 0.3mol), be suitable for heating of electrically heated cover and insulation at 200-220 ℃, reacted 5 hours.Under the decompression of 2000-1000Pa, 58-60 ℃ cut is collected in rectifying, gets product 48.7 grams, and by gas chromatographic analysis, 3-chloro-4-fluoride trifluoro toluene content is 98.5% in the product, and yield is 79%.Mother liquor after the rectification under vacuum is filtered, remove the salt of distillation mother liquor, under the decompression decompression of 2000-1500Pa, reclaim tetramethylene sulfone then.
Embodiment 4
Present embodiment is used to illustrate the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention.
In 500 milliliters of four-hole boiling flasks with agitator, thermometer, pressure warning unit and rectifying column, add exsiccant tetramethylene sulfone 200 grams, anhydrous potassium fluoride 53.3 gram (content 98%, 0.9mol), the cuprous chloride of 0.05 gram and the 15-hat-5 of 0.05 gram, add the back and feed nitrogen, make and remain nitrogen atmosphere in the flask, under agitation add 3 then, 4-two chlorobenzotrifluorides 65.2 gram (content 99%, 0.3mol), be suitable for heating of electrically heated cover and insulation at 210-220 ℃, reacted 20 hours.Under the decompression of 2000-1000Pa, 58-60 ℃ cut is collected in rectifying, gets product 46.8 grams, and by gas chromatographic analysis, 3-chloro-4-fluoride trifluoro toluene content is 97% in the product, yield 76%.Mother liquor after the rectification under vacuum is filtered, remove the salt of distillation mother liquor, under the decompression decompression of 2000-1500Pa, reclaim tetramethylene sulfone then.
Embodiment 5
Present embodiment is used to illustrate the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention.
Method according to embodiment 1 prepares 3-chloro-4-fluoride trifluoro toluene, and different is that cuprous chloride is replaced by the cuprous bromide of identical weight, reacts 20 hours.Under the decompression of 2000-1000Pa, 58-60 ℃ cut is collected in rectifying, gets product 47.4 grams, and by gas chromatographic analysis, 3-chloro-4-fluoride trifluoro toluene content is 96% in the product, yield 77%.Mother liquor after the rectification under vacuum is filtered, remove the salt of distillation mother liquor, under the decompression decompression of 2000-1500Pa, reclaim dimethyl sulfoxide (DMSO) then.
Embodiment 6
Present embodiment is used to illustrate the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention.
Method according to embodiment 1 prepares 3-chloro-4-fluoride trifluoro toluene, and different is 15-hat-5 replacements of 18-hat-6 by identical weight, reacts 20 hours.Under the decompression of 2000-1000Pa, 58-60 ℃ cut is collected in rectifying, gets product 46.8 grams, and by gas chromatographic analysis, 3-chloro-4-fluoride trifluoro toluene content is 97% in the product, yield 76%.Mother liquor after the rectification under vacuum is filtered, remove the salt of distillation mother liquor, under the decompression decompression of 2000-1500Pa, reclaim dimethyl sulfoxide (DMSO) then.
Embodiment 7
Present embodiment is used to illustrate the preparation method of 3-chloro-4-fluoride trifluoro toluene of the present invention.
Method according to embodiment 1 prepares 3-chloro-4-fluoride trifluoro toluene, and different is that catalyzer replaces with the cuprous chloride of 0.8 gram and the 18-hat-6 of 0.1 gram, reacts 20 hours.Under the decompression of 2000-1000Pa, 58-60 ℃ cut is collected in rectifying, gets product 47.1 grams, and by gas chromatographic analysis, 3-chloro-4-fluoride trifluoro toluene content is 97% in the product, and yield is 76.5%.Mother liquor after the rectification under vacuum is filtered, remove the salt of distillation mother liquor, under the decompression decompression of 2000-1500Pa, reclaim dimethyl sulfoxide (DMSO) then.
Claims (10)
1. the preparation method of a 3-chloro-4-fluoride trifluoro toluene, it is characterized in that this preparation method is included under the existence of catalyzer, makes 3,4-two chlorobenzotrifluorides and anhydrous potassium fluoride carry out fluoridation in polar aprotic solvent, described catalyzer contains the halogenide and the crown ether of copper.
2. preparation method according to claim 1, wherein, with described 3, the weight of 4-two chlorobenzotrifluorides is benchmark, described catalyst consumption is 0.1-3 weight %.
3. preparation method according to claim 1, wherein, in described catalyzer, the halogenide of described copper and the weight ratio 1-10 of described crown ether: 1.
4. according to claim 1 or 3 described preparation methods, wherein, in described catalyzer, the halogenide of described copper is cuprous chloride.
5. preparation method according to claim 1, wherein, in described catalyzer, described crown ether be selected from 15-hat-5,18-hat-6 and bicyclohexane also-at least a in the 18-hat-6.
6. preparation method according to claim 1, wherein, described polar aprotic solvent and described 3, the weight ratio of 4-two chlorobenzotrifluorides is 1-5: 1.
7. according to claim 1 or 6 described preparation methods, wherein, described polar aprotic solvent is to be selected from least a in dimethyl sulfoxide (DMSO), tetramethylene sulfone, N-Methyl pyrrolidone and the N,N-dimethylacetamide.
8. preparation method according to claim 1, wherein, described fluoridation is carried out under inert atmosphere, and described inert atmosphere is to be selected from least a in nitrogen, helium, neon, argon gas and the radon gas.
9. preparation method according to claim 1, wherein, the condition of described fluoridation comprises: described 3, the mol ratio of 4-two chlorobenzotrifluorides and described anhydrous potassium fluoride is 1: 2-10, temperature of reaction is 150-230 ℃, the reaction times is 1-30 hour.
10. preparation method according to claim 1, wherein, this preparation method also is included in and carries out rectification under vacuum after described fluoridation finishes.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106554289A (en) * | 2015-09-24 | 2017-04-05 | 江苏扬农化工股份有限公司 | A kind of method that non-metal catalyst prepares fluorine amine cyanogen chrysanthemumic acid |
| CN111187180A (en) * | 2018-11-15 | 2020-05-22 | 江苏优士化学有限公司 | Method for recycling tetrafluoroterephthalonitrile synthetic wastewater |
| CN114560774A (en) * | 2020-11-27 | 2022-05-31 | 瑞博(杭州)医药科技有限公司 | Synthetic method of 2-fluoro-3-nitrobenzoic acid |
-
2010
- 2010-06-04 CN CN2010101983331A patent/CN102267871A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106554289A (en) * | 2015-09-24 | 2017-04-05 | 江苏扬农化工股份有限公司 | A kind of method that non-metal catalyst prepares fluorine amine cyanogen chrysanthemumic acid |
| CN111187180A (en) * | 2018-11-15 | 2020-05-22 | 江苏优士化学有限公司 | Method for recycling tetrafluoroterephthalonitrile synthetic wastewater |
| CN114560774A (en) * | 2020-11-27 | 2022-05-31 | 瑞博(杭州)医药科技有限公司 | Synthetic method of 2-fluoro-3-nitrobenzoic acid |
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Application publication date: 20111207 |