CN105017320B - The method preparing the double salt of two fluoro ethyl salt/1,2 vinyls under condition of no solvent - Google Patents
The method preparing the double salt of two fluoro ethyl salt/1,2 vinyls under condition of no solvent Download PDFInfo
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- CN105017320B CN105017320B CN201510381754.0A CN201510381754A CN105017320B CN 105017320 B CN105017320 B CN 105017320B CN 201510381754 A CN201510381754 A CN 201510381754A CN 105017320 B CN105017320 B CN 105017320B
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- 0 *C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 Chemical compound *C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 0.000 description 8
- RZXMPPFPUUCRFN-UHFFFAOYSA-N Cc(cc1)ccc1N Chemical compound Cc(cc1)ccc1N RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 3
- GEHNEHXOFJLIQZ-NSCUHMNNSA-N C/C=C/C(C1c(cc2)ccc2N)C1c(cc1)ccc1N Chemical compound C/C=C/C(C1c(cc2)ccc2N)C1c(cc1)ccc1N GEHNEHXOFJLIQZ-NSCUHMNNSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Cc1ccc(C)cc1 Chemical compound Cc1ccc(C)cc1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N Cc1ccccc1OC Chemical compound Cc1ccccc1OC DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to preparing two fluoro ethyl salt/1 under a kind of condition of no solvent, the simple and easy method of the double salt of 2 vinyls, under condition of no solvent, by organophosphors and difluoro ethylating agent or the mixing of vinylated reagent, stirring reaction 0.5~36h at 20~150 DEG C, after the completion of question response, washs solid, filter, gained solid oil pump is drying to obtain product.The method has good substrate applicability, simple to operate, the easy purification of product, advantages of environment protection.By the structure adjusting reaction temperature and change organic phosphine, the preparation of two fluoro ethyl salt in same system, can also be realized, two fluoro ethyl salt are a class potentially fluorine-containing strippings and slicings, are expected to be used for the synthesis of multiple fluorochemicals.
Description
Technical field
The invention belongs to organic synthesiss, medicine, pesticide and field of functional materials are and in particular under a kind of condition of no solvent
Prepare the simple and easy method of the double salt of two fluoro ethyl salt/1,2- vinyl.
Background technology
Quaternary salt has been obtained for being widely applied in chemistry, the field such as biology, material.Quaternary salt can be used as phase transfer and urges
Agent and the multiple chemical reaction of Lewis acid catalyst.Quaternary salt with active α-H can be used as phosphorus ylide precursor,
In the presence of alkali, aldehyde, ketone can be changed into by corresponding alkene by Wittig reaction.Additionally, the larger aryl quaternary salt of volume
There is good chemical stability, fat-soluble and crystallinity, when their aniones special with structure form new ion salt, its
Originally the stability of anion, dissolubility and crystallinity can be greatly improved.The ionic liquid being made up of quaternary salt, also
Can serve as solvent and the material that can be recycled, meet the requirement of Green Chemistry.At present, in order to meet from industry-by-industry
Application demand, the novel salt of a large amount of structures is by synthetic.
Two cationes are connected by the double salt of trans 1,2- vinyl by a vinyl, and at two cationes
Antiposition in double bond.The double salt of 1,2- vinyl is easy to hydrolysis and alcoholysis in the basic conditions;1,2- vinyl is double
Cation in salt can also be by tert-butyl group anion nucleophilic displacement of fluorine;And with I-And Ph4B-1,2- vinyl for anion
Double (triphenyl) salt can serve as the additive of fire proofing material.These interesting phenomenons imply the double salt of 1,2- vinyl also
There are much potential, abundant property value must excavate.There is several methods that synthesis of trans 1 at present, the double salt of 2- vinyl, but
It is because their the substrate scope of application is narrower, need using the reagent to air or water sensitive, raw materials used synthesis is time-consuming
(such as:[IC≡CI][OTf]2(E)-R1R2PCH=CHPR1R2), therefore significantly limit their application.
Content of the invention
It is an object of the invention to provide it is double to prepare two fluoro ethyl salt/trans 1,2- vinyl under a kind of condition of no solvent
The simple and easy method of salt, the method wide application range of substrates, agents useful for same is insensitive to air and water, and raw material sources are simple, operation
Simplicity, yield is higher, and does not have solvent to participate in, environmental friendliness.
The present invention solves the scheme that adopted of above-mentioned technical problem:Two fluoro ethyl salt/1 are prepared under condition of no solvent,
The method of the double salt of 2- vinyl it is characterised in that:Under condition of no solvent, by organophosphors and difluoro ethylating agent or ethylene
Base reagent mixes, and wherein organophosphors and the mol ratio of difluoro ethylating agent or vinylated reagent are 1:0.2~5, in -20
Stirring reaction 0.5~36h at~150 DEG C, after the completion of question response, washs solid, filters, gained solid oil pump is drying to obtain product
Product.
By such scheme, the formula of two described fluoro ethyl salt is:
Wherein, R1、R2、R3And R4、R5、R6For identical or different group, selected from phenyl, p-methylphenyl, a tolyl, neighbour
Tolyl, p-methoxyphenyl, m-methoxyphenyl, guaiacyl, rubigan, a chlorphenyl, Chloro-O-Phenyl, to fluorophenyl,
Between fluorophenyl, adjacent fluorophenyl, p-trifluoromethyl phenyl, m-trifluoromethylphenyl, o-trifluoromethyl phenyl, 4- xenyl, 3- joins
Phenyl, 2- xenyl, cyclohexyl, methyl, any one in ethyl, propyl group, butyl and the tert-butyl group, wherein X are RfnSO3、
RSO3、ArSO3、RfnCO2、RCO2、ArCO2, Cl, Br or I;RfnFluoroalkyl for 1~8 carbon or perfluoroalkyl, R is 1~4
The alkyl of carbon, Ar is phenyl, p-methylphenyl, p-nitrophenyl and five fluorine, tetrafluoro, trifluoro, in difluoro or single fluorine substituted-phenyl
Any one.
By such scheme, the formula of the double salt of described 1,2- vinyl is:
Wherein, R1、R2、R3、R4、R5、R6For identical or different group, selected from phenyl, p-methylphenyl, a tolyl, right
Anisyl, m-methoxyphenyl, rubigan, a chlorphenyl, to fluorophenyl, a fluorophenyl, p-trifluoromethyl phenyl, a trifluoro
Aminomethyl phenyl, 4- xenyl, 3- xenyl, 2- xenyl, cyclohexyl, methyl, arbitrary in ethyl, propyl group, butyl and the tert-butyl group
Kind, wherein X is RfnSO3、RSO3、ArSO3、RfnCO2、RCO2、ArCO2, Cl, Br or I;RfnFluoroalkyl or complete for 1~8 carbon
Fluoroalkyl, R is the alkyl of 1~4 carbon, and Ar is phenyl, p-methylphenyl, p-nitrophenyl and five fluorine, tetrafluoro, trifluoro, difluoro
Or any one in list fluorine substituted-phenyl.
By such scheme, the general structure of described organophosphors is:
Wherein, R1、R2、R3And R4、R5、R6For identical or different group, selected from phenyl, p-methylphenyl, a tolyl, neighbour
Tolyl, p-methoxyphenyl, m-methoxyphenyl, guaiacyl, rubigan, a chlorphenyl, Chloro-O-Phenyl, to fluorophenyl,
Between fluorophenyl, adjacent fluorophenyl, p-trifluoromethyl phenyl, m-trifluoromethylphenyl, o-trifluoromethyl phenyl, 4- xenyl, 3- joins
Phenyl, 2- xenyl, cyclohexyl, methyl, in ethyl, propyl group, butyl and the tert-butyl group any one.
By such scheme, the general structure of described difluoro ethylating agent or vinylated reagent is
Wherein X is RfnSO3、RSO3、ArSO3、RfnCO2、RCO2、ArCO2, Cl, Br or I;RfnFluoroalkyl for 1~8 carbon
Or perfluoroalkyl, R is the alkyl of 1~4 carbon, Ar is phenyl, p-methylphenyl, p-nitrophenyl and five fluorine, tetrafluoro, trifluoro,
Any one in difluoro or single fluorine substituted-phenyl.
Preparation method of the present invention, can be respectively obtained by the structure adjusting reaction temperature and change organic phosphine
Two fluoro ethyl salt and the double salt of 1,2- vinyl.
When using relatively low reaction temperature, all of organic phosphine is completely converted into two fluoro ethyl salt;Raise reaction temperature
Degree, two fluoro ethyl salt can continue to be transformed into the double salt of 1,2- vinyl.For triaryl phosphine, replace when ortho position is had on phenyl ring
During base, even if at high temperature, reaction also stays at two fluoro ethyl salt phases, and (triaryl phosphine refers to one of organic phosphine class
Type).
The present invention prepares two fluoro ethyl salt and the double reaction used by salt of 1,2- vinyl, it is recommended to use following equation
Represent:
R1、R2、R3, R4、R5、R6And X, with above-mentioned definition.
Two fluoro ethyl salt of present invention synthesis, its typical structure is:
The double salt of 1,2- vinyl of present invention synthesis, its typical structure is:
The present invention utilizes the gentle, XCH to air-stable2CF2H reagent and organic phosphine reaction, under condition of no solvent,
Prepare the double salt of trans 1,2- vinyl.Compared with other synthetic methods, the method has good substrate applicability, simple to operate,
The easy purification of product, advantages of environment protection.By the structure adjusting reaction temperature and change organic phosphine, in same system
In, the preparation of two fluoro ethyl salt can also be realized, two fluoro ethyl salt are a class potentially fluorine-containing strippings and slicings, are expected to be used for multiple
The synthesis of fluorochemical.
Specific embodiment
Will be helpful to understand the present invention by following embodiments, but be not intended to limit present disclosure.
Embodiment 1:(counterparty's formula 1)
By TfOCH2CF2H (0.514g, 2.4mmol) is mixed with triphenylphosphine (0.525g, 2mmol), anti-in 120 DEG C of stirrings
Answer 24h, after question response system is cooled to room temperature, gained solid ether, toluene, normal hexane or petroleum ether, filter, then use
Oil pump is drained, and obtains final product product (E)-[Ph3PCH=CHPPh3][OTf]2(white solid, 0.66g, 0.78mmol), yield:
78%.1H NMR(CD3COCD3):δ 8.71 (t, J=20.7Hz, 2H), 8.04 (t, J=7.2Hz, 6H), 7.95 (m, 12H),
7.88(m,12H).19F NMR(CD3COCD3):δ-78.8(s,6F).31P NMR(CD3COCD3):δ20.8(s).
Embodiment 2:(counterparty's formula 1)
By TfOCH2CF2H (0.514g, 2.4mmol) is mixed with tricyclohexyl phosphine (1.346g, 4.8mmol), stirs in 120 DEG C
Mix reaction 8h, after question response system is cooled to room temperature, gained solid ether, toluene, normal hexane or petroleum ether, filter,
Drained with oil pump again, obtain final product product (E)-[(C6H11)3PCH=CHP (C6H11)3][OTf]2(white solid, 1.335g,
1.51mmol), yield:63%.1H NMR:δ 8.03 (t, J=18.1Hz, 2H), 3.08 (m, 6H), 2.02-1.84 (m, 30H),
1.64-1.53(m,24H),1.26(m,6H).19F NMR:δ-78.3(s,6F).31P NMR:δ33.0(s).
Embodiment 3:(counterparty's formula 2)
By TfOCH2CF2H (0.257g, 1.2mmol) is mixed with tricyclohexyl phosphine (0.337g, 1.2mmol), at room temperature
Stirring reaction 12h, then gained solid ether, toluene, normal hexane or petroleum ether, filters, then is drained with oil pump, obtain final product
Product [(C6H11)3PCH2CF2H] [OTf] (white solid, 0.325g, 0.66mmol) yield:55%.1H NMR:δ6.48
(tdt, J=55.4Hz, J=13.9Hz, J=3.3Hz, 1H), 3.20 (m, 2H), 2.53 (q, J=12.4Hz, 3H), 2.01-
1.95(m,12H),1.86-1.81(m,3H),1.61-1.54(m,6H),1.46-1.38(m,6H),1.36-1.28(m,3H)
.19F NMR:δ -78.4 (s, 3F), -107.5 (dm, J=55.6Hz, 2F).31P NMR:δ32.9(s).
Embodiment 4:(counterparty's formula 1)
By TfOCH2CF2H (0.257g, 1.2mmol) is mixed with three (p-methylphenyl) phosphine (0.365g, 1.2mmol), in 120
Stirring reaction 6h at DEG C, then gained solid ether, toluene, normal hexane or petroleum ether, filter, then drained with oil pump,
Obtain final product product (E)-[(4-CH3C6H4)3PCH=CHP (4-CH3C6H4)3][OTf]2(white solid, 0.390g, 0.42mmol) produces
Rate:70%.1H NMR:δ 8.04 (t, J=20.7Hz, 2H), 7.59-7.53 (m, 24H), 2.51 (s, 18H).19F NMR:δ-
78.4(s,6F).31P NMR:δ20.9(s).
Embodiment 5:(counterparty's formula 1)
By TfOCH2CF2H (0.257g, 1.2mmol) and three (tolyl) phosphine (0.365g, 1.2mmol) mixes, in 120
Stirring reaction 6h at DEG C, then gained solid ether, toluene, normal hexane or petroleum ether, filter, then drained with oil pump,
Obtain final product product (E)-[(3-CH3C6H4)3PCH=CHP (3-CH3C6H4)3][OTf]2(white solid, 0.447g, 0.48mmol) produces
Rate:80%.1H NMR:δ 8.23 (t, J=20.7Hz, 2H), 7.66-7.60 (m, 12H), 7.53-7.47 (m, 12H), 2.45
(s,18H).19F NMR:δ-78.6(s,6F).31P NMR:δ20.5(s).
Embodiment 6:(counterparty's formula 2)
By TfOCH2CF2H (0.257g, 1.2mmol) is mixed with three (o-tolyl) phosphine (0.365g, 1.2mmol), in 120
Stirring reaction 6h at DEG C, then gained solid ether, toluene, normal hexane or petroleum ether, filter, then drained with oil pump,
Obtain final product product [(2-CH3C6H4)3PCH2CF2H] [OTf] (white solid, 0.306g, 0.59mmol) yield:49%.1H NMR:δ
7.75-7.68 (m, 6H), 7.55-7.48 (m, 6H), 6.41 (tdt, J=55.0Hz, J=14.6Hz, J=2.9Hz, 1H),
4.34 (q, J=14.1Hz, 2H), 2.24 (s, 9H).19F NMR:δ -78.4 (s, 3F), -109.5 (dm, J=55.0Hz, 2F)
.31P NMR:δ19.2(s).
Embodiment 7:(counterparty's formula 1)
By ICH2CF2H (0.192g, 1.0mmol) is mixed with triphenylphosphine (0.262g, 1.0mmol), stirs at 120 DEG C
Reaction 24h, then gained solid ether, toluene, normal hexane or petroleum ether, filters, then is drained with oil pump, obtain final product product
(E)-[Ph3PCH=CHPPh3]I2(yellow solid, 0.349g, 0.43mmol) yield:87%.1H NMR:δ 8.71 (t, J=
21.1Hz, 2H), 8.04 (t, J=7.2Hz, 6H), 7.95 (m, 12H), 7.88 (m, 12H).31P NMR(CD3COCD3):δ20.8
(s).
Embodiment 8:(counterparty's formula 1)
By TsOCH2CF2H (0.236g, 1.0mmol) is mixed with triphenylphosphine (0.262g, 1.0mmol), stirs at 120 DEG C
Mix reaction 24h, then gained solid ether, toluene, normal hexane or petroleum ether, filter, then drained with oil pump, obtain final product product
Product (E)-[Ph3PCH=CHPPh3][OTs]2(light yellow solid, 0.221g, 0.25mmol) yield:50%.1H NMR:δ8.49
(t, J=21.1Hz, 2H), 7.82-7.76 (m, 12H), 7.74-7.65 (m, 12H), 7.55-7.52 (m, 6H), 7.50-7.46
(m,8H),2.17(s,6H).
Embodiment 9:(counterparty's formula 1)
By CF3COOCH2CF2H (0.356g, 2.0mmol) is mixed with triphenylphosphine (0.525g, 2.0mmol), in 120 DEG C
Lower stirring reaction 24h, then gained solid ether, toluene, normal hexane or petroleum ether, filters, then is drained with oil pump, that is,
Obtain product (E)-[Ph3PCH=CHPPh3][OCOCF3]2(light yellow solid, 0.038g, 0.05mmol) yield:5%.1H NMR:
δ 8.46 (t, J=21.1Hz, 2H), 7.81 (t, J=7.3Hz, 6H), 7.75-7.71 (m, 12H), 7.69-7.66 (m, 12H).19F NMR:δ-75.6(s,6F).
Embodiment 10:(counterparty's formula 2)
By TfOCH2CF2H (0.107g, 0.5mmol) is mixed with tri-n-butyl phosphine (0.101g, 0.5mmol), at room temperature
Stirring reaction 6h, then gained liquid ether, toluene, normal hexane or petroleum ether, filters, then is drained with oil pump, obtain final product
Product [(t-Bu)3PCH2CF2H] [OTf] (colourless liquid, 0.162g, 0.39mmol) yield:78%.1H NMR(CDCl3):δ
6.39 (tdt, J=55.2Hz, J=13.7Hz, J=3.3Hz, 1H), 3.30-3.11 (m, 2H), 2.45-2.22 (m, 6H),
1.73-1.37 (m, 12H), 0.98 (dt, J=12.6Hz, J=7.0Hz, 9H).19F NMR(CDCl3):δ-78.4(s,3F),-
107.5 (dm, J=55.6Hz, 2F).
Embodiment 11:(counterparty's formula 3)
By [Ph3PCH2CF2H] [OTf] (0.238g, 0.5mmol) and three (p-methylphenyl) phosphine (0.152g, 0.5mmol) mix
Close, stirring reaction 6h at 120 DEG C, then gained solid ether, toluene, normal hexane or petroleum ether, filter, then with oily
Pumping is done, and obtains final product product (E)-[(4-CH3C6H4)3PCH=CHPPh3] [OTf] [F] (light yellow solid, 0.104g,
0.12mmol) yield:48%.1H NMR:δ 8.00 (t, J=21.0Hz, 2H), 7.74-7.70 (m, 12H), 7.60-7.54 (m,
15H),2.50(s,9H).19F NMR:δ-78.6(s,3F),-137.3(s,1F).
Embodiment 12:(counterparty's formula 3)
By [Ph3PCH2CF2H] [OTf] (0.238g, 0.5mmol) and three (p-methoxyphenyl) phosphine (0.176g, 0.5mmol)
Mixing, stirring reaction 6h at 120 DEG C, then gained solid ether, toluene, normal hexane or petroleum ether, filters, then uses
Oil pump is drained, and obtains final product product (E)-[(4-CH3OC6H4)3PCH=CHPPh3] [OTf] [F] (light yellow solid, 0.161g,
0.17mmol) yield:68%.1H NMR:δ 8.00 (t, J=21.3Hz, 2H), 7.90-7.79 (m, 6H), 7.77-7.66 (m,
12H),7.61-7.56(m,9H),3.96(s,9H).19F NMR:δ-75.6(s,6F),-137.3(s,1F).
Claims (2)
1. under condition of no solvent the double salt of preparation 1,2- vinyl method it is characterised in that:Under condition of no solvent, will be organic
Phosphorus and the mixing of vinylated reagent, wherein organophosphors are 1 with the mol ratio of vinylated reagent:0.2~5, in -20~150 DEG C
Lower stirring reaction 0.5~36h, after the completion of question response, washs solid, filters, gained solid oil pump is drying to obtain product;Described
The general structure of vinylated reagent be
Wherein X is RfnSO3、RSO3、ArSO3、RfnCO2、RCO2、ArCO2, Cl, Br or I;RfnFor the fluoroalkyl of 1~8 carbon, R is
The alkyl of 1~4 carbon, Ar is phenyl, p-methylphenyl, p-nitrophenyl and five fluorine, tetrafluoro, trifluoro, difluoro or single fluorine replace
Any one in phenyl;
The formula of the double salt of described 1,2- vinyl is:
Wherein, R1、R2、R3、R4、R5、R6For identical or different group, selected from phenyl, p-methylphenyl, a tolyl, to methoxy
Phenyl, m-methoxyphenyl, rubigan, a chlorphenyl, to fluorophenyl, a fluorophenyl, p-trifluoromethyl phenyl, m-trifluoromethyl
Phenyl, 4- xenyl, 3- xenyl, 2- xenyl, cyclohexyl, methyl, in ethyl, propyl group, butyl and the tert-butyl group any one, its
Middle X is RfnSO3、RSO3、ArSO3、RfnCO2、RCO2、ArCO2, Cl, Br or I;RfnFor the fluoroalkyl of 1~8 carbon, R is 1~4
The alkyl of carbon, Ar is phenyl, p-methylphenyl, p-nitrophenyl and five fluorine, tetrafluoro, trifluoro, in difluoro or single fluorine substituted-phenyl
Any one.
2. method according to claim 1 is it is characterised in that the general structure of described organophosphors is:
Wherein, R1、R2、R3And R4、R5、R6For identical or different group, selected from phenyl, p-methylphenyl, a tolyl, to methoxy
Phenyl, m-methoxyphenyl, rubigan, a chlorphenyl, to fluorophenyl, a fluorophenyl, p-trifluoromethyl phenyl, m-trifluoromethyl
Phenyl, 4- xenyl, 3- xenyl, 2- xenyl, cyclohexyl, methyl, in ethyl, propyl group, butyl and the tert-butyl group any one.
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CN103374033A (en) * | 2012-04-24 | 2013-10-30 | 宁波大学 | Functionalized quaternary phosphonium salt ionic liquid of organic phosphine and preparation method thereof |
CN102702258A (en) * | 2012-06-21 | 2012-10-03 | 南开大学 | Water removal method for quaternary phosphonium salt aqueous solution |
CN104710475A (en) * | 2013-12-13 | 2015-06-17 | 微宏动力系统(湖州)有限公司 | Preparation method of quaternary phosphonium salt |
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