CN107973693A - A kind of method for synthesizing trifluoro aryl ethylene class compound - Google Patents
A kind of method for synthesizing trifluoro aryl ethylene class compound Download PDFInfo
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- CN107973693A CN107973693A CN201610932354.9A CN201610932354A CN107973693A CN 107973693 A CN107973693 A CN 107973693A CN 201610932354 A CN201610932354 A CN 201610932354A CN 107973693 A CN107973693 A CN 107973693A
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- trifluoro
- iodine
- ethylene
- trifluorostyrene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
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- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention relates to a kind of method for synthesizing trifluoro aryl ethylene class compound, belong to the field of chemical synthesis.The method of the invention reacts generation trifluoro aryl ethylene class compound with the salt compounded of iodine being conveniently easy to get under the proper conditions using trifluoro-ethylene as starting material.Synthetic method provided by the invention has the characteristics that universality is wide, the reaction time is short, easy to operate compared with conventional method, because of the advantages that its is of low cost, technique is simple, pollution is small, is expected to realize industrialized production.
Description
Technical field
The present invention relates to chemosynthesis technical field, and in particular to a kind of side for synthesizing trifluoro aryl ethylene class compound
Method.
Background technology
Trifluoro-ethylene (Trifluoroethylene, abbreviation TrFE or HFC-1123) is used as in Organic fluoride industry and produces four
The accessory substance of vinyl fluoride, is typically directly incinerated, and not only polluted environment but also wastes raw material.The present invention is exactly to use work
The exhaust gas that industry production tetrafluoroethene produces prepares trifluoro aryl ethylene class compound for raw material.Trifluorostyrene therein (α,
β, β-trifluorostyerene, abbreviation TFS) a kind of fluorochemical monomer is used as, available for preparing fluoropolymer.The Type of Collective
Thing has the characteristics that radiation hardness, heat-resisting, dissolubility is good, transparency is high, economize on electricity loss is low.
Fluorinated aryl ethene is in structure due to the introducing of fluorine atom so that the tridimensional electronic property of reaction site and reaction
Property all become complicated.Synthesis for trifluoro aryl ethylene class compound can trace back to the forties in last century, and Cohen et al. is adopted
Be raw material with aromatic ring, through friedel-crafts acylation, carbonyl chlorination, fluorine halogen exchange, zinc powder reduction dehalogenation and etc. be prepared for trifluoro-benzene second
Alkene [Cohen S.G.；Wolosinski H.T.；Scheuer P.J.J.Am.Chem.Soc.2002,71,3439-3440.],
But it the method use the reagents such as poisonous phosphorus pentachloride, it is difficult to suitable for industrialized production.
Patent US 2,874,166 is reported has synthesized trifluorostyrene with phenyl lithium and tetrafluoroethene, although this method line
Road is succinct, but has used highly active phenyl lithium, it is therefore desirable to reaction system anhydrous and oxygen-free, while phenyl lithium is due to activity
The too high compatibility that also limit fragrant ring substituents, easily generates substantial amounts of accessory substance.2011, Masato O. et al. into
The reaction of the direct attack tetrafluoroethene of phenyl-magnesium-chloride of having gone, and obtain medium yield [Masato O.；Tadashi K；
Tsubasa H；Hiroki S；Ryohei D；Sensuke O.J.Am.Chem.Soc.2011,133,3256-3259.].2012
Year, three Ai Fu companies of Shanghai are reported one kind in 103708988 A of patent CN and are existed using phenyl-magnesiumhalide and excessive tetrafluoroethene
Control the method that trifluorostyrene is prepared under low temperature.Using the method for Grignard Reagent, although can be easier to obtain product,
Still it is easy to cause the generation of one-pass attack accessory substance.
2012, Chinese Academy of Sciences's Shanghai Institute of Organic Chemistry was in patent CN 102241554, CN 102532202, with trifluoro chlorine (bromine)
With gentle nucleopilic reagent phenyl boric acid cross-coupling reaction occurs under palladium chtalyst for ethene, and a step prepares trifluorostyrene and derivative
Thing.This method uses the palladium of costliness to be unfavorable for industrialization for catalytic reagent.
Either a variety of synthetic method severe reaction conditions recited above, or cost of material increases, it is difficult to realize big rule
Mould produces.
The content of the invention
To solve the above problems, the present invention provides, a kind of reaction condition is gentle, of low cost, easy to operate, universality is wide,
The method of the high synthesis trifluoro aryl ethylene class compound of yield.
To achieve the above object, present invention selection is made in a mild condition using trifluoroethane and salt compounded of iodine as starting material
Standby trifluoro aryl ethylene class compound.
Specifically, the present invention provides a kind of method for synthesizing trifluoro aryl ethylene class compound, and the method is：With trifluoro
Ethene and salt compounded of iodine are reacted for raw material, and trifluoro aryl ethylene class compound is prepared.
Preferably, the cationic moiety of the salt compounded of iodine is di (hetero) aryl iodide cation or diaryl iodonium cation,
Preferably diaryl iodonium cation；The anionicsite of the salt compounded of iodine is non-nucleophilic anion or nucleophilicity anion,
Preferably non-nucleophilic anion.
Preferably, the salt compounded of iodine is diphenyl iodine fluoroform sulphonate, 1,3- bis- (2- thiophene) iodine fluoroform sulphur
One kind in hydrochlorate and diphenyl iodine nitrate, is preferably diphenyl iodine fluoroform sulphonate.
Preferably, the molar feed ratio of the trifluoro-ethylene and the salt compounded of iodine is 1:0.1~1:5, it is preferably 1:1-3,
More preferably 1:1.5.
Preferably, the trifluoro-ethylene is reacted with the salt compounded of iodine under the action of metallic catalyst and alkali.
Preferably, the metallic catalyst is A races (main group), the metal salt of B races (subgroup), is preferably IB races metal salt,
More preferably copper metal salt.
Preferably, the amount of metal catalyst is 1~100mol% equivalents (relative to trifluoro-ethylene), is preferably 3-
20mol%, more preferably 5mol%.
Preferably, the alkali is organic base or inorganic base, is preferably inorganic base, more preferably potassium hydroxide.
Preferably, the dosage of the alkali is 0.1~10 equivalent (equivalent to trifluoro-ethylene), is preferably 1-3 equivalents, more preferably
For 1.5 equivalents.
Preferably, the reaction carries out in nonpolar solvent or polar solvent, is preferably polar solvent, and more preferably two
Methylformamide (DMF).
Preferably, the reaction temperature is 20 DEG C~160 DEG C, is preferably 60-120 DEG C, more preferably 100 ± 5 DEG C.
Preferably, when the reaction time of the trifluoro-ethylene and the salt compounded of iodine is 0.1-48 small, when being preferably 2-12 small,
More preferably 6 ± 0.5 it is small when.
The synthetic route of the method for synthesis trifluoro aryl ethylene class compound of the present invention is as follows：
Wherein, substrate 1 is reactant trifluoro-ethylene, and substrate 2 is salt compounded of iodine, and product 3 is trifluoro aryl ethylene class compound.
Preferably, the separation that the method for synthesis trifluoro aryl ethylene class compound of the present invention is further included to product carries
It is pure, be specially：The trifluoro-ethylene and the salt compounded of iodine remove solvent, rejoin low boiling point solvent, remove after the reaction was complete
Metallic catalyst and alkali, separate, after concentration to obtain the final product.
Preferably, the low boiling point solvent is nonpolar solvent, more preferably dichloromethane.
Preferably, separation uses column chromatography or recrystallization after the concentration, more preferably using column chromatography.
Beneficial effects of the present invention：
Compared with prior art, the present invention its remarkable advantage is：Reaction condition it is simple it is gentle, of low cost, easy to operate,
It is of low cost, universality is wide, environmental pollution is small, be expected to realize industrialization large-scale production.
Embodiment
Following embodiments are used to illustrate the present invention, but are not limited to the scope of the present invention.Unless otherwise specified, embodiment
In used reagent be conventional commercial reagent.For example, diphenyl iodine fluoroform sulphonate, 1,3- bis- (2- thiophene) iodine three
Fluorine mesylate and diphenyl iodine nitrate can be prepared by this area conventional method；Copper acetate monohydrate, acetic acid
Magnesium and DMF are purchased from Chengdu Ke Long Chemical Co., Ltd.s；Technological means used is those skilled in the art institute in embodiment
Well known conventional means.
Embodiment 1：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), described method includes following steps：
(1) by trifluoro-ethylene 820mg, diphenyl iodine fluoroform sulphonate 6.45g, potassium hydroxide 840g, a hydration vinegar
Sour copper 100mg, solvent polarity solvent DMF 20mL are mixed to join in reactor, are heated to 100 DEG C, when reaction 6 is small；
(2) DMF is removed after reaction, uses CH2Cl2Dissolve and filter and remove catalyst and alkali, column chromatography method and purify
To solid trifluorostyrene (3a) (1.45g), yield 92%.
Embodiment 2：The synthesis of 2- trifluorovinyls (3b)
The present embodiment provides a kind of method of synthesis 2- trifluorovinyls (3b), the method is same as Example 1,
Differ only in：Diphenyl iodine fluoroform sulphonate (6.45g) is replaced with into 1,3- bis- (2- thiophene) iodine trifluoromethanesulfonic acid
Salt (6.63g)；
Product obtained by the present embodiment is 2- trifluorovinyls (3b), its yield is 84%.
Embodiment 3：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：Diphenyl iodine fluoroform sulphonate (6.45g) is replaced with into diphenyl iodine nitrate (3.43g)；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 32%.
Embodiment 4：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：Copper acetate monohydrate is replaced with into magnesium acetate (71mg)；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 24%.
Embodiment 5：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：It is 2.0g by the increase of copper acetate monohydrate dosage；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 92%.
Embodiment 6：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：Potassium hydroxide is replaced with into potassium ethoxide (1.26g)；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 91%.
Embodiment 7：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：Potassium hydroxide dosage is reduced to 84g；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 8%.
Embodiment 8：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：The increase of potassium hydroxide dosage is 8.4g
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 92%.
Embodiment 9：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：Solvent polarity solvent DMF is replaced with into non-solvent polar solvent toluene 20mL；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 25%.
Embodiment 10：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：Temperature is reduced to 20 DEG C；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 40%.
Embodiment 11：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：It it is 160 DEG C by temperature rise；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 92%.
Embodiment 12：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：Diphenyl iodine fluoroform sulphonate dosage is reduced to 430mg)；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 8%.
Embodiment 13：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：It is 21.5g by the dosage increase of diphenyl iodine fluoroform sulphonate；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 92%.
Embodiment 14：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：To be reduced in the reaction time 0.1 it is small when；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 7%.
Embodiment 15：The synthesis of trifluorostyrene (3a)
The present embodiment provides a kind of method of synthesis trifluorostyrene (3a), the method is same as Example 1, and difference is only
It is：To increase in the reaction time for 48 it is small when；
Product obtained by the present embodiment is trifluorostyrene (3a), its yield is 93%.
Although above with general explanation and specific embodiment, the present invention is described in detail, at this
On the basis of invention, it can be made some modifications or improvements, this will be apparent to those skilled in the art.Therefore,
These modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to the scope of protection of present invention.
Claims (10)
- A kind of 1. method for synthesizing trifluoro aryl ethylene class compound, it is characterised in that using trifluoro-ethylene and salt compounded of iodine as raw material Carry out reaction and trifluoro aryl ethylene class compound is prepared.
- 2. according to the method described in claim 1, it is characterized in that, the cationic moiety of the salt compounded of iodine is di (hetero) aryl iodide Cation or diaryl iodonium cation, are preferably diaryl iodonium cation；It is preferably non-nucleophilic and/or the anionicsite of the salt compounded of iodine is nucleophilicity anion or non-nucleophilic anion Anion.
- 3. according to the method any one of claim 1-2, it is characterised in that the trifluoro-ethylene and the salt compounded of iodine Molar feed ratio is 1:0.1~1:5, it is preferably 1:1-3.
- 4. method according to any one of claim 1-3, it is characterised in that the trifluoro-ethylene exists with the salt compounded of iodine Reacted under the action of metallic catalyst and alkali.
- 5. according to the method described in claim 4, it is characterized in that, the metallic catalyst for A races or B races metal salt, it is excellent IB races metal salt is selected, more preferably copper metal salt；And/or relative to trifluoro-ethylene, the dosage of the metallic catalyst is 1~100mol% equivalents, is preferably 3- 20mol%.
- 6. it is preferably inorganic base according to the method described in claim 4, it is characterized in that, the alkali is organic base or inorganic base, More preferably potassium hydroxide；And/or relative to trifluoro-ethylene, the dosage of the alkali is 0.1~10 equivalent, is preferably 1-3 equivalents.
- 7. according to the method described in claim 4, it is characterized in that, it is described reaction carried out in nonpolar or polar solvent, it is excellent Elect polar solvent as, more preferably DMF.
- 8. according to claim 1-7 any one of them methods, it is characterised in that the reaction temperature is 20 DEG C~160 DEG C, excellent Elect 60-120 DEG C as, more preferably 100 ± 5 DEG C；And/or the reaction time of the vinyl fluoride and the salt compounded of iodine for 0.1-48 it is small when, when being preferably 2-12 small, more preferably For 6 ± 0.5 it is small when.
- 9. according to claim 1-8 any one of them methods, it is characterised in that further include the separating-purifying to product, specifically For：The trifluoro-ethylene and the salt compounded of iodine remove solvent, rejoin low boiling point solvent and urged with removing metal after the reaction was complete Agent and alkali, separate, after concentration to obtain the final product.
- 10. according to the method described in claim 9, it is characterized in that, the low boiling point solvent is nonpolar solvent, more preferably Dichloromethane；And/or separation uses column chromatography or recrystallization after the concentration, more preferably using column chromatography.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112624898A (en) * | 2019-09-24 | 2021-04-09 | 中昊晨光化工研究院有限公司 | Synthetic method of aryl trifluoroethylene compound |
| CN112811974A (en) * | 2019-11-18 | 2021-05-18 | 中昊晨光化工研究院有限公司 | Novel aryl trifluoroethylene synthesized by arylation reagent and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102241554A (en) * | 2011-04-22 | 2011-11-16 | 中国科学院上海有机化学研究所 | Method for synthesizing trifluorostyrene fluorine-containing monomer |
| CN102532202A (en) * | 2011-12-20 | 2012-07-04 | 中国科学院上海有机化学研究所 | Palladium complex containing trichlorethylene, synthesizing method and application of palladium complex to trifluorovinylation |
| CN103708988A (en) * | 2012-09-29 | 2014-04-09 | 上海三爱富新材料股份有限公司 | Synthetic method of [alpha],[beta],[beta]-trifluorostyrene type compounds |
-
2016
- 2016-10-25 CN CN201610932354.9A patent/CN107973693B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241554A (en) * | 2011-04-22 | 2011-11-16 | 中国科学院上海有机化学研究所 | Method for synthesizing trifluorostyrene fluorine-containing monomer |
| CN102532202A (en) * | 2011-12-20 | 2012-07-04 | 中国科学院上海有机化学研究所 | Palladium complex containing trichlorethylene, synthesizing method and application of palladium complex to trifluorovinylation |
| CN103708988A (en) * | 2012-09-29 | 2014-04-09 | 上海三爱富新材料股份有限公司 | Synthetic method of [alpha],[beta],[beta]-trifluorostyrene type compounds |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112624898A (en) * | 2019-09-24 | 2021-04-09 | 中昊晨光化工研究院有限公司 | Synthetic method of aryl trifluoroethylene compound |
| CN112624898B (en) * | 2019-09-24 | 2022-03-22 | 中昊晨光化工研究院有限公司 | Synthetic method of aryl trifluoroethylene compound |
| CN112811974A (en) * | 2019-11-18 | 2021-05-18 | 中昊晨光化工研究院有限公司 | Novel aryl trifluoroethylene synthesized by arylation reagent and preparation method thereof |
| CN112811974B (en) * | 2019-11-18 | 2022-03-22 | 中昊晨光化工研究院有限公司 | Novel aryl trifluoroethylene synthesized by arylation reagent and preparation method thereof |
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