CN114438530B - Electrochemical preparation method of (Z) -3-amino-2-bromobut-2-enenitrile - Google Patents
Electrochemical preparation method of (Z) -3-amino-2-bromobut-2-enenitrile Download PDFInfo
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Abstract
The invention discloses an electrochemical preparation method of (Z) -3-amino-2-bromobut-2-dinitrile, and belongs to the technical field of electrochemical organic synthesis. The preparation method comprises the following steps: electrolyte, sodium triflate, tetra-n-butyl ammonium bromide, a sulfur ylide reagent and hexafluoroisopropanol are added into an electrolytic cell without a diaphragm, an electrolytic solvent is inserted into an anode and a cathode, stirring is carried out, the electric conduction is carried out, the reaction is carried out under the constant current condition, after the reaction is finished, the organic solvent is used for carrying out organic extraction on the electrolyte, and then the (Z) -3-amino-2-bromobut-2-acrylonitrile is obtained through separation and purification. The method of the invention only uses cheap and easily available tetra-n-butyl ammonium bromide and acetonitrile as raw materials, and prepares the (Z) -3-amino-2-bromobut-2-dinitrile by using an electrochemical synthesis means. The whole reaction process has mild condition, is simple and easy to operate, has little pollution and accords with the concept of green chemistry.
Description
Technical Field
The invention belongs to the field of electrochemical synthesis, and relates to a preparation method of (Z) -3-amino-2-bromobut-2-dinitrile, in particular to an electrochemical preparation method of (Z) -3-amino-2-bromobut-2-dinitrile.
Background
The organic nitrile compounds have broad-spectrum biological activity, are widely used in medicines, pesticides and natural products, and are important components in medicine synthesis, material science and fine chemicals. Meanwhile, the cyano functional group is an important multifunctional group in organic synthesis, can be used as a precursor of various functional groups, can be used for conversion of aldehyde, ketone, amine, amidine, amide and heterocycle, and has important application value in organic synthesis. The existing method for synthesizing the organic nitrile compound mainly comprises the following steps: (1) Transition metal catalyzed C-H cyanation reactions, but such processes typically require the use of stoichiometric amounts of toxic metal cyanides (e.g., TMSCN, KCN, cuCN, etc.) as cyano sources; (2) By using electrophilic CN + C-H cyanation reactions using reagents as Cyano sources, such as the preparation of 3-cyanoindoles using 5- (Cyano) dibenzothiophene triflate as Cyano source (5- (cyanoo) dibenzothiophenium Triflate: A Sulfur-Based Reagent for Electrophilic Cyanation and cyantetracyclic methods, angew. Chem. Int. Ed.2019,58, 9496-9500), but such methods require either the preparation of the cyanating reagents or the use of an excess of base;in addition, NH 4 I/DMF,NH 4 HCO 3 /DMSO,TMEDA/(NH 4 ) 2 CO 3 ) The synthesis of organic nitriles as cyano sources has also been reported, but such methods also require the use of excess amounts of oxidizing agent and the reaction to be carried out at higher temperatures. Simple alkyl nitrile (such as acetonitrile) is introduced into target molecules to synthesize some complex organic nitrile compounds, and besides the characteristics of atom economy and environmental protection, a convenient way is provided for further modifying molecules and synthesizing various active compounds. However, such methods as reported so far often require the use of metal catalysts, chemical oxidants, or higher reaction temperatures. Therefore, the development of a green and efficient method for synthesizing the organic nitrile compound has important significance.
In addition, the bromo-compound is used as a common intermediate for organic synthesis, and has important application in organic synthesis, and can directly perform a series of coupling reactions (such as Ullmann reaction, heck reaction, negishi reaction and Stille reaction) with alkene, terminal alkyne, amine, halogenated aromatic hydrocarbon, organic metal compound and the like to form a C-C bond and a C-hetero bond under the catalysis of a transition metal catalyst. Bromine atoms can effectively change the spatial structure of the compound, thereby changing the physical property, chemical property and physiological activity of the compound and enabling the bromide to have some functional uses. The introduction of bromine atoms in the drug molecule can improve its properties: the bromohydrocarbon medicine has the advantages of strong antibacterial capability, good bactericidal effect, good stability, low toxicity, no skin irritation and corrosion, can inhibit the assembly of tubulin related to cancer, can inhibit aldose reductase related to diabetic complications, and lipase related to asthma, etc. And many bromine-containing compounds have excellent flame retardant properties and can be used for producing flame retardants. Therefore, the bromide has a small effect on the production of fine chemical products such as medicines, flame retardants, pesticides, fuels and the like. However, the method of preparing the bromo compound is generally such that the halogen undergoes electrophilic substitution with the organic compound. However, this method has many disadvantages: the halogen toxicity is higher, and the risk coefficient is higher; the hydrogen halide produced is susceptible to corrosion of the metal equipment; the atom utilization rate is low; poor selectivity, etc. In response to these shortcomings, scientists have made further improvements, such as with NBS. But still has the following disadvantages: the atom utilization rate is low; the succinimide byproduct produced is more difficult to remove. Scientists are inspired by the enzyme-catalyzed oxidative bromination reaction, and the bromination reaction of aromatic hydrocarbon is carried out by using hydrogen halide and some oxidants together, but the reaction system is complex and expensive oxidants are required to be used.
The (Z) -3-amino-2-bromobut-2-dinitrile not only has the functional group structures of the two compounds, namely bromine atoms and cyano groups, but also has the functional groups such as double bonds, amino groups and the like, which are contained in the compounds, and has great application value in organic synthesis. However, the synthesis work of (Z) -3-amino-2-bromobut-2-enenitrile has not been reported. Therefore, the development of a simple and environment-friendly method for synthesizing (Z) -3-amino-2-bromobut-2-enenitrile is of great significance.
Disclosure of Invention
The invention provides a preparation method for synthesizing (Z) -3-amino-2-bromobut-2-dinitrile under electrochemical conditions.
The invention utilizes electrochemical organic synthesis means, uses cheap and safe n-tetrabutylammonium bromide as a bromine source and acetonitrile as a cyano source, and successfully synthesizes the (Z) -3-amino-2-bromobut-2-dinitrile. The compound can complete a series of derivative conversion through functional groups such as cyano groups, bromine atoms, double bonds, amino groups and the like contained in the structure, can synthesize more compounds with important values, has the characteristics of atom economy and environmental protection, provides a convenient way for further modifying molecules to synthesize various active compounds, and has great synthesis application value. Meanwhile, the whole reaction process has mild conditions, is simple and easy to operate, has little pollution and accords with the concept of green chemistry.
The synthetic route of the invention is as follows:
wherein CF is as follows 3 SO 3 Na is sodium trifluoromethane sulfonate, HFIP is hexafluoroisopropanol, ACN is acetonitrile, and electroyte isAn electrolyte.
The invention is realized by the following technical scheme.
An electrochemical preparation method of (Z) -3-amino-2-bromobut-2-dinitrile, comprising the following steps:
(1) Adding tetra-n-butyl ammonium bromide and a solvent into a diaphragm-free electrolytic cell, and then adding a sulfur ylide reagent, sodium triflate, an electrolyte and hexafluoroisopropanol;
(2) Inserting an electrode into the reaction liquid, stirring at room temperature, and electrifying for reaction until the raw materials are completely reacted;
(3) Extracting, concentrating, separating and purifying the reaction liquid to obtain (Z) -3-amino-2-bromobut-2-dinitrile.
Further, the sulforeed reagent of step (1) is 2- (dimethyl (oxo) -sulfinyl) -1-phenylethan-1-one.
Further, the molar ratio of tetra-n-butyl ammonium bromide to the sulfur ylide reagent in step (1) is 1:2.
Further, the molar ratio of the sodium triflate to the tetra-n-butyl ammonium bromide in the step (1) is 3:1-4:1.
Preferably, the molar ratio of sodium triflate to tetra-n-butyl ammonium bromide in step (1) is 4:1.
Further, the electrolyte in the step (1) is tetra-n-butyl ammonium perchlorate, tetra-n-butyl ammonium tetrafluoroborate or tetra-n-butyl ammonium hexafluorophosphate.
Preferably, the electrolyte of step (1) is tetra-n-butyl ammonium perchlorate.
Further, the solvent in the step (1) is acetonitrile.
Further, the volume ratio of the amount of the electrolyte substance and the solvent in the step (1) was 0.1mmol/mL.
Further, the molar ratio of hexafluoroisopropanol to tetra-n-butyl ammonium bromide in the step (1) is 2:1-3:1.
Preferably, the molar ratio of hexafluoroisopropanol to tetra-n-butylammonium bromide in step (1) is 2:1.
Further, the electrode in the step (2) is: a carbon rod anode and a platinum sheet cathode.
Preferably, in step (2), the anode is a carbon rod (d=5 mm) and the cathode is a 10mm×15mm×0.1mm platinum sheet.
Further, the cathode and anode distances of the electrodes in the step (2) are 10mm.
Further, the current intensity of the energizing reaction in the step (2) is 5mA.
Further, the time of the electrifying reaction in the step (2) is 4-5h.
Preferably, the time of the energizing reaction in the step (2) is 5 hours.
The invention has the following advantages and beneficial effects:
(1) The invention promotes the reaction by cleaning reagent-electrons through electrochemical means, avoids using stoichiometric traditional oxidant, thereby avoiding the discharge of various wastes and reducing environmental pollution.
(2) The electrode used in the invention is a common inert electrode, does not need electrode modification, and does not have the problem of metal anode consumption.
(3) The invention does not need to add metal catalyst and chemical oxidant, thereby effectively avoiding the use of expensive, toxic and harmful additives to the environment, and being environment-friendly.
(4) The invention has mild condition, no need of high temperature, simple and easy operation and low cost, and the whole operation process only needs to lead direct current to the traditional stirring reaction device for reaction at room temperature.
(5) The method only takes the cheap and easily obtained tetra-n-butyl ammonium bromide (bromine source) and acetonitrile (cyano source) as raw materials, and the whole reaction process has mild conditions, is simple and easy to implement, has small pollution and accords with the concept of green chemistry.
Drawings
FIG. 1 shows the target product (Z) -3-amino-2-bromobut-2-enenitrile prepared in accordance with an embodiment of the present invention 1 H NMR spectrum.
FIG. 2 shows the target product (Z) -3-amino-2-bromobut-2-enenitrile prepared in accordance with an embodiment of the present invention 13 C NMR spectrum.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but embodiments of the present invention are not limited thereto.
Example 1
Into a 5mL round bottom flask was charged 33mg (0.1 mmol) tetra-n-butylammonium bromide Bu 4 NBr,5mL of solvent acetonitrile ACN, then 40mg (0.2 mmol) of thioylide reagent 2- (dimethyl (oxo) -sulfinyl) -1-phenylethan-1-one, 70mg (0.4 mmol) of sodium triflate CF are added 3 SO 3 Na,34mg (0.2 mmol) hexafluoroisopropanol HFIP and 171mg (0.1 mmol/mL) of electrolyte tetra-n-butyl ammonium perchlorate. An electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode) is inserted, a direct current power supply supplies 5mA, and stirring reaction is carried out for 5h. After the reaction, the solvent of the reaction solution was removed by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. Times.3), the organic layers were combined, and saturated NaCl solution (20 mL. Times.1) was washed with water, anhydrous Na 2 SO 4 Drying, evaporating under reduced pressure, and separating to obtain the target product (Z) -3-amino-2-bromobut-2-dinitrile with a yield of 90%.
The reaction route of this example is as follows:
example 2
The reaction route of this example was the same as that of example 1.
Into a 5mL round bottom flask was charged 33mg (0.1 mmol) tetra-n-butylammonium bromide Bu 4 NBr,5mL of solvent acetonitrile ACN, then 40mg (0.2 mmol) of thioylide reagent 2- (dimethyl (oxo) -sulfinyl) -1-phenylethan-1-one, 70mg (0.4 mmol) of sodium triflate CF are added 3 SO 3 Na,34mg (0.2 mmol) hexafluoroisopropanol HFIP and 171mg (0.1 mmol/mL) of electrolyte tetra-n-butyl ammonium perchlorate. An electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode) is inserted, a direct current power supply supplies 5mA, and stirring reaction is carried out for 4 hours. After the reaction, the solvent of the reaction solution was removed by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. Times.3), the organic layers were combined, and saturated NaCl solution (20 mL. Times.1) was washed with water, anhydrous Na 2 SO 4 Drying, evaporating under reduced pressure, separating to obtain target product (Z) -3-amino-2-bromobut-2-dinitrile, yield 78％。
Example 3
The reaction route of this example was the same as that of example 1.
Into a 5mL round bottom flask was charged 33mg (0.1 mmol) tetra-n-butylammonium bromide Bu 4 NBr,5mL of solvent acetonitrile ACN, then 40mg (0.2 mmol) of thioylide reagent 2- (dimethyl (oxo) -sulfinyl) -1-phenylethan-1-one, 70mg (0.4 mmol) of sodium triflate CF are added 3 SO 3 Na,34mg (0.2 mmol) hexafluoroisopropanol HFIP and 194mg (0.1 mmol/mL) of electrolyte tetra-n-butyl ammonium hexafluorophosphate. An electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode) is inserted, a direct current power supply supplies 5mA, and stirring reaction is carried out for 5h. After the reaction, the solvent of the reaction solution was removed by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. Times.3), the organic layers were combined, and saturated NaCl solution (20 mL. Times.1) was washed with water, anhydrous Na 2 SO 4 Drying, evaporating under reduced pressure, and separating to obtain the target product (Z) -3-amino-2-bromobut-2-dinitrile with a yield of 32%.
Example 4
The reaction route of this example was the same as that of example 1.
Into a 5mL round bottom flask was charged 33mg (0.1 mmol) tetra-n-butylammonium bromide Bu 4 NBr,5mL of solvent acetonitrile ACN, then 40mg (0.2 mmol) of thioylide reagent 2- (dimethyl (oxo) -sulfinyl) -1-phenylethan-1-one, 70mg (0.4 mmol) of sodium triflate CF are added 3 SO 3 Na,34mg (0.2 mmol) hexafluoroisopropanol HFIP and 165mg (0.1 mmol/mL) of the electrolyte tetra-n-butyl ammonium tetrafluoroborate. An electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode) is inserted, a direct current power supply supplies 5mA, and stirring reaction is carried out for 5h. After the reaction, the solvent of the reaction solution was removed by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. Times.3), the organic layers were combined, and saturated NaCl solution (20 mL. Times.1) was washed with water, anhydrous Na 2 SO 4 Drying, evaporating under reduced pressure, and separating to obtain the target product (Z) -3-amino-2-bromobut-2-dinitrile with a yield of 31%.
Example 5
The reaction route of this example was the same as that of example 1.
Into a 5mL round bottom bottle was added 33mg (0.1 mmol) of tetra-n-butylAmmonium bromide Bu 4 NBr,5mL of solvent acetonitrile ACN, then 40mg (0.2 mmol) of thioylide reagent 2- (dimethyl (oxo) -sulfinyl) -1-phenylethan-1-one, 70mg (0.4 mmol) of sodium triflate CF are added 3 SO 3 Na,51mg (0.3 mmol) hexafluoroisopropanol HFIP and 171mg (0.1 mmol/mL) of electrolyte tetra-n-butyl ammonium perchlorate. An electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode) is inserted, a direct current power supply supplies 5mA, and stirring reaction is carried out for 5h. After the reaction, the solvent of the reaction solution was removed by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. Times.3), the organic layers were combined, and saturated NaCl solution (20 mL. Times.1) was washed with water, anhydrous Na 2 SO 4 Drying, evaporating under reduced pressure, and separating to obtain the target product (Z) -3-amino-2-bromobut-2-dinitrile with a yield of 48%.
Example 6
The reaction route of this example was the same as that of example 1.
Into a 5mL round bottom flask was charged 33mg (0.1 mmol) tetra-n-butylammonium bromide Bu 4 NBr,5mL of solvent acetonitrile ACN, then 40mg (0.2 mmol) of thioylide reagent 2- (dimethyl (oxo) -sulfinyl) -1-phenylethan-1-one, 53mg (0.3 mmol) of sodium triflate CF are added 3 SO 3 Na,34mg (0.2 mmol) hexafluoroisopropanol HFIP and 171mg (0.1 mmol/mL) of electrolyte tetra-n-butyl ammonium perchlorate. An electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode) is inserted, a direct current power supply supplies 5mA, and stirring reaction is carried out for 5h. After the reaction, the solvent of the reaction solution was removed by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. Times.3), the organic layers were combined, and saturated NaCl solution (20 mL. Times.1) was washed with water, anhydrous Na 2 SO 4 Drying, evaporating under reduced pressure, and separating to obtain the target product (Z) -3-amino-2-bromobut-2-dinitrile with a yield of 62%.
The target product (Z) -3-amino-2-bromobut-2-enenitrile obtained in the above example 1 The H NMR spectrum is shown in FIG. 1, and the identification data are: 1 H NMR(500MHz,CDCl 3 )δ4.95(s,2H),2.19(s,3H).
the target product (Z) -3-amino-2-bromobut-2-enenitrile obtained in the above example 13 The C NMR spectrum is shown in FIG. 2, and the identification data are: 13 C NMR(126MHz,CDCl 3 )δ155.0,118.5,57.8,19.4.
the above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (6)
1. A method for the electrochemical preparation of (Z) -3-amino-2-bromobut-2-enenitrile, comprising the steps of:
(1) Adding tetra-n-butyl ammonium bromide and a solvent into a diaphragm-free electrolytic cell, and then adding a sulfur ylide reagent, sodium triflate, an electrolyte and hexafluoroisopropanol;
(2) Inserting an electrode into the reaction liquid, stirring at room temperature, and electrifying for reaction until the raw materials are completely reacted;
(3) Extracting, concentrating, separating and purifying the reaction liquid to obtain (Z) -3-amino-2-bromobut-2-dinitrile;
the sulfur ylide reagent in the step (1) is 2- (dimethyl (oxo) -sulfinyl) -1-phenylethan-1-one;
the electrolyte in the step (1) is tetra-n-butyl ammonium perchlorate, tetra-n-butyl ammonium tetrafluoroborate or tetra-n-butyl ammonium hexafluorophosphate;
the solvent in the step (1) is acetonitrile;
the current intensity of the electrifying reaction in the step (2) is 5mA, and the electrifying reaction time is 4-5h.
2. The process for the electrochemical preparation of (Z) -3-amino-2-bromobut-2-enenitrile according to claim 1, characterized in that the molar ratio of tetra-n-butylammonium bromide to sulfolobus-led reagent in step (1) is 1:2.
3. The method for electrochemical preparation of (Z) -3-amino-2-bromobut-2-enenitrile according to claim 1, characterized in that the molar ratio of sodium triflate to tetra-n-butylammonium bromide in step (1) is 3:1-4:1.
4. The method for electrochemical preparation of (Z) -3-amino-2-bromobut-2-enenitrile according to claim 1, characterized in that the ratio of the amount of the electrolyte substance to the volume of the solvent in step (1) is 0.1mmol/mL.
5. The method for electrochemical preparation of (Z) -3-amino-2-bromobut-2-enenitrile according to claim 1, characterized in that the molar ratio of hexafluoroisopropanol to tetra-n-butylammonium bromide in step (1) is 2:1-3:1.
6. The method for electrochemical preparation of (Z) -3-amino-2-bromobut-2-enenitrile according to claim 1, characterized in that the electrode of step (2) is: a carbon rod anode and a platinum sheet cathode.
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