CN114438530A - Electrochemical preparation method of (Z) -3-amino-2-bromobut-2-alkene nitrile - Google Patents
Electrochemical preparation method of (Z) -3-amino-2-bromobut-2-alkene nitrile Download PDFInfo
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Abstract
The invention discloses an electrochemical preparation method of (Z) -3-amino-2-bromobutyl-2-alkene nitrile, belonging to the technical field of electrochemical organic synthesis. The preparation method comprises the following steps: adding electrolyte, sodium trifluoromethanesulfonate, tetra-n-butyl ammonium bromide, a sulfur ylide reagent and hexafluoroisopropanol into a diaphragm-free electrolytic cell, inserting an electrolytic solvent into an anode and a cathode, stirring, electrifying, reacting under a constant current condition, after the reaction is finished, carrying out organic extraction on the electrolyte by using an organic solvent, and then separating and purifying to obtain (Z) -3-amino-2-bromobut-2-enenitrile. The method only uses cheap and easily obtained tetra-n-butylammonium bromide and acetonitrile as raw materials to prepare the (Z) -3-amino-2-bromobut-2-alkene nitrile by an electrochemical synthesis means. The whole reaction process is mild in condition, simple and feasible, and low in pollution, and accords with the concept of green chemistry.
Description
Technical Field
The invention belongs to the field of organic electrochemical synthesis, relates to a preparation method of (Z) -3-amino-2-bromobutyl-2-alkene nitrile, and particularly relates to an electrochemical preparation method of (Z) -3-amino-2-bromobutyl-2-alkene nitrile.
Background
The organic nitrile compounds have broad-spectrum biological activity, are widely present in medicines, pesticides and natural products, and are important components in drug synthesis, material science and fine chemicals. At the same time, cyanogenThe radical functional group is an important multifunctional functional group in organic synthesis, can be used as a precursor of various functional groups, can be used for converting aldehydes, ketones, amines, amidines, amides and heterocycles, and has important application value in organic synthesis. The existing methods for synthesizing organic nitrile compounds mainly comprise 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 the cyano source; (2) by using electrophilic CN+C-H Cyanation reaction using a Reagent as a Cyano source, such as the preparation of 3-cyanoindole compounds (5- (cyanoo) dibenzothiophene Triflate: A sulfurr-Based Reagent for electrochemical Cyanation and cyanocatalysis. Angew. chem. int. Ed. 2019,58, 9496-well 9500) using 5- (Cyano) dibenzothiophene Triflate as a Cyano source, but such methods require the preparation of a Cyanation Reagent or the use of an excess of a base; furthermore, NH4I/DMF,NH4HCO3/DMSO,TMEDA/(NH4)2CO3) The synthesis of organic nitriles as sources of cyano groups has also been reported, but such processes also require the use of excess oxidizing agents and the reaction is 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, the method also provides a convenient way for further modifying molecules and synthesizing various active compounds. However, the methods 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 is of great significance.
In addition, the bromide is used as a common organic synthesis intermediate, has important application in organic synthesis, and can directly generate a series of coupling reactions (such as Ullmann reaction, Heck reaction, Negishi reaction and Stille reaction) with olefin, terminal alkyne, amine, halogenated aromatic hydrocarbon, organic metal compound and the like to form C-C bonds and C-hybrid bonds under the catalysis of a transition metal catalyst. Bromine atoms can effectively change the spatial structure of a compound, thereby changing the physical property, chemical property and physiological activity of the compound, and enabling the bromide to have some functional purposes. The introduction of bromine atoms into the drug molecule can improve its properties: the brominated hydrocarbon medicine has the advantages of strong bacteriostatic ability, good bactericidal effect, good stability, low toxicity, no irritation to skin, no corrosiveness, capability of inhibiting the assembly of tubulin related to cancer, capability of inhibiting aldose reductase related to diabetic complications, capability of inhibiting lipoxygenase related to asthma and the like. And many bromine-containing compounds have excellent flame retardant property and can be used for producing flame retardants. Therefore, the role of bromides in the production of fine chemical products such as medicines, flame retardants, pesticides, and fuels is not insignificant. However, the process for preparing the bromides is generally an electrophilic substitution of the halogen with an organic compound. However, this method has many disadvantages: the halogen toxicity is high, and the danger coefficient is high; the hydrogen halide produced is susceptible to corrosion of metal equipment; the atom utilization rate is low; poor selectivity, etc. To address these shortcomings, scientists have made further improvements, such as with NBS. There are still deficiencies: the atom utilization rate is low; the succinimide by-product produced is more difficult to remove. Scientists have inspired enzymatic oxidative bromination reactions, which use hydrogen halides in combination with some oxidizing agents to carry out the bromination of aromatic hydrocarbons, but the reaction system is complicated and requires the use of expensive oxidizing agents.
The (Z) -3-amino-2-bromobut-2-alkene nitrile not only has the functional group structures of the two compounds, namely bromine atom and cyano, but also has larger application value in organic synthesis of double bonds, amino and other functional groups contained in the compounds. However, no work has been reported on the synthesis of (Z) -3-amino-2-bromobut-2-enenitrile. Therefore, it is of great significance to develop a simple and environmentally friendly method for synthesizing (Z) -3-amino-2-bromobut-2-enenitrile.
Disclosure of Invention
The invention provides a preparation method for synthesizing (Z) -3-amino-2-bromobutyl-2-alkene nitrile under electrochemical conditions.
The method successfully synthesizes the (Z) -3-amino-2-bromobut-2-alkene nitrile by using an electrochemical organic synthesis means, using cheap and safe n-tetrabutylammonium bromide as a bromine source and acetonitrile as a cyano source. The compound can complete a series of derivative transformation through functional groups such as cyano-group, bromine atom, double bond and amino contained in the structure, can synthesize more compounds with important value, has the characteristics of atom economy and environmental protection, provides a convenient way for further modifying molecules and synthesizing various active compounds, and has great synthesis and application values. Meanwhile, the whole reaction process is mild in condition, simple and feasible, and low in pollution, and accords with the concept of green chemistry.
The synthetic scheme of the invention is as follows:
wherein, CF3SO3Na is sodium trifluoromethanesulfonate, HFIP is hexafluoroisopropanol, ACN is acetonitrile, and electrolyte is electrochyte.
The invention is realized by the following technical scheme.
A method for electrochemically preparing (Z) -3-amino-2-bromobut-2-enenitrile, comprising the following steps:
(1) adding tetra-n-butylammonium bromide and a solvent into a diaphragm-free electrolytic cell, and then adding a sulfur ylide reagent, sodium trifluoromethanesulfonate, an electrolyte and hexafluoroisopropanol;
(2) inserting an electrode into the reaction solution, stirring at room temperature, and electrifying for reaction until the raw materials react completely;
(3) and (Z) -3-amino-2-bromobutyl-2-alkene nitrile is obtained by extracting, concentrating, separating and purifying the reaction liquid.
Further, the thioylide reagent of step (1) is 2- (dimethyl (oxo) -sulfenyl) -1-phenylethane-1-one.
Further, the mole ratio of the tetra-n-butylammonium bromide to the sulfur ylide reagent in the step (1) is 1: 2.
Further, the molar ratio of the sodium trifluoromethanesulfonate to the tetra-n-butylammonium bromide in the step (1) is 3:1-4: 1.
Preferably, the molar ratio of the sodium trifluoromethanesulfonate to the tetra-n-butylammonium bromide in the 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 in the step (1) is tetra-n-butyl ammonium perchlorate.
Further, the solvent in the step (1) is acetonitrile.
Further, the ratio of the amount of the substance of the electrolyte and the volume of the solvent in the step (1) is 0.1 mmol/mL.
Further, the molar ratio of the hexafluoroisopropanol to the tetra-n-butylammonium bromide in the step (1) is 2:1-3: 1.
Preferably, the molar ratio of the hexafluoroisopropanol to the 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, the anode in the step (2) is a carbon rod (d ═ 5mm), and the cathode is a platinum sheet of 10mm × 15mm × 0.1 mm.
Further, the distance between the cathode and the anode of the electrode in the step (2) is 10 mm.
Further, the current intensity of the electrifying reaction in the step (2) is 5 mA.
Further, the time of the electrifying reaction in the step (2) is 4-5 h.
Preferably, the time of the electrifying reaction in the step (2) is 5 h.
The invention has the following advantages and beneficial effects:
(1) the invention promotes the reaction by cleaning reagent-electrons through an electrochemical means, and avoids using a stoichiometric traditional oxidant, thereby avoiding the discharge of various wastes and reducing the environmental pollution.
(2) The electrode used in the invention is a common inert electrode, electrode modification is not needed, and the problem of consumption of a metal anode is also solved.
(3) The invention does not need to add metal catalyst and chemical oxidant, thereby effectively avoiding using expensive, toxic and environmentally harmful additives, and being green, environment-friendly and environment-friendly.
(4) The invention has mild condition, does not need high temperature, only needs to be electrified with direct current to react at room temperature in the whole operation process on the traditional stirring reaction device, is simple and easy to implement and has low cost.
(5) The method only uses cheap and easily-obtained tetra-n-butylammonium bromide (bromine source) and acetonitrile (cyanogen source) as raw materials, and the whole reaction process has mild conditions, is simple and feasible, has little pollution and accords with the concept of green chemistry.
Drawings
FIG. 1 shows the preparation of the target product (Z) -3-amino-2-bromobut-2-enenitrile according to the example of the present invention1H NMR spectrum.
FIG. 2 shows the preparation of (Z) -3-amino-2-bromobut-2-enenitrile, the target product13C NMR spectrum.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the present invention is not limited thereto.
Example 1
To a 5mL round bottom flask was added 33mg (0.1mmol) of tetra-n-butylammonium bromide Bu4NBr, 5mL of the solvent acetonitrile ACN, followed by 40mg (0.2mmol) of the thioylide reagent 2- (dimethyl (oxo) -sulfenyl) -1-phenylethane-1-one, 70mg (0.4mmol) of sodium trifluoromethanesulfonate CF3SO3Na, 34mg (0.2mmol) of hexafluoroisopropanol HFIP and 171mg (0.1 mmol/mL) of the electrolyte tetra-n-butylammonium perchlorate. Inserting an electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode), supplying 5mA with a direct current power supply, and stirring for reaction for 5 hours. After the reaction, the solvent was removed from the reaction mixture by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. times.3), the organic layers were combined, washed with saturated NaCl solution (20 mL. times.1) and anhydrous Na2SO4Drying, decompressing and evaporating to dryness, and separating to obtain the target product (Z) -3-amino-2-bromobutyl-2-alkene nitrile with the yield of 90 percent.
The reaction scheme of this example is as follows:
example 2
The reaction scheme of this example is the same as example 1.
To a 5mL round bottom flask was added 33mg (0.1mmol) of tetra-n-butylammonium bromide Bu4NBr, 5mL of the solvent acetonitrile ACN, followed by 40mg (0.2mmol) of the thioylide reagent 2- (dimethyl (oxo) -sulfenyl) -1-phenylethane-1-one, 70mg (0.4mmol) of sodium trifluoromethanesulfonate CF3SO3Na, 34mg (0.2mmol) of hexafluoroisopropanol HFIP and 171mg (0.1 mmol/mL) of the electrolyte tetra-n-butylammonium perchlorate. Inserting an electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode), supplying 5mA with a direct current power supply, and stirring for reaction for 4 hours. After the reaction, the solvent was removed from the reaction mixture by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. times.3), the organic layers were combined, washed with saturated NaCl solution (20 mL. times.1) and anhydrous Na2SO4Drying, decompressing and evaporating to dryness, and separating to obtain the target product (Z) -3-amino-2-bromobutyl-2-alkene nitrile with the yield of 78 percent.
Example 3
The reaction scheme of this example is the same as example 1.
To a 5mL round bottom flask was added 33mg (0.1mmol) of tetra-n-butylammonium bromide Bu4NBr, 5mL of the solvent acetonitrile ACN, followed by 40mg (0.2mmol) of the thioylide reagent 2- (dimethyl (oxo) -sulfenyl) -1-phenylethane-1-one, 70mg (0.4mmol) of sodium trifluoromethanesulfonate CF3SO3Na, 34mg (0.2mmol) hexafluoroisopropanol HFIP and 194mg (0.1 mmol/mL) of the electrolyte tetra-n-butyl ammonium hexafluorophosphate. Inserting an electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode), supplying 5mA with a direct current power supply, and stirring for reaction for 5 hours. After the reaction, the solvent was removed from the reaction mixture by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. times.3), the organic layers were combined, washed with saturated NaCl solution (20 mL. times.1) and anhydrous Na2SO4Drying, decompressing and evaporating to dryness, and separating to obtain the target product (Z) -3-amino-2-bromobutyl-2-alkene nitrile with the yield of 32 percent.
Example 4
The reaction scheme of this example is the same as example 1.
To a 5mL round bottom flask was added 33mg (0.1 m)mol) tetra-n-butylammonium bromide Bu4NBr, 5mL of the solvent acetonitrile ACN, followed by 40mg (0.2mmol) of the thioylide reagent 2- (dimethyl (oxo) -sulfenyl) -1-phenylethane-1-one, 70mg (0.4mmol) of sodium trifluoromethanesulfonate CF3SO3Na, 34mg (0.2mmol) of hexafluoroisopropanol HFIP and 165mg (0.1 mmol/mL) of the electrolyte tetra-n-butylammonium tetrafluoroborate. Inserting an electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode), supplying 5mA with a direct current power supply, and stirring for reaction for 5 hours. After the reaction, the solvent was removed from the reaction mixture by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. times.3), the organic layers were combined, washed with saturated NaCl solution (20 mL. times.1) and anhydrous Na2SO4Drying, decompressing and evaporating to dryness, and separating to obtain the target product (Z) -3-amino-2-bromobutyl-2-alkene nitrile with the yield of 31 percent.
Example 5
The reaction scheme of this example is the same as example 1.
To a 5mL round bottom flask was added 33mg (0.1mmol) of tetra-n-butylammonium bromide Bu4NBr, 5mL of the solvent acetonitrile ACN, followed by 40mg (0.2mmol) of the thioylide reagent 2- (dimethyl (oxo) -sulfenyl) -1-phenylethane-1-one, 70mg (0.4mmol) of sodium trifluoromethanesulfonate CF3SO3Na, 51mg (0.3mmol) of hexafluoroisopropanol HFIP and 171mg (0.1 mmol/mL) of the electrolyte tetra-n-butylammonium perchlorate. Inserting an electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode), supplying 5mA with a direct current power supply, and stirring for reaction for 5 hours. After the reaction, the solvent was removed from the reaction mixture by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. times.3), the organic layers were combined, washed with saturated NaCl solution (20 mL. times.1) and anhydrous Na2SO4Drying, decompressing and evaporating to dryness, and separating to obtain the target product (Z) -3-amino-2-bromobutyl-2-alkene nitrile with the yield of 48 percent.
Example 6
The reaction scheme of this example is the same as example 1.
To a 5mL round bottom flask was added 33mg (0.1mmol) of tetra-n-butylammonium bromide Bu4NBr, 5mL of acetonitrile ACN as solvent, followed by 40mg (0.2mmol) of thioylide reagent 2- (dimethyl (oxo) -sulfenyl) -1-phenylethane-1-one, 53mg (0.3mmol) of sodium trifluoromethanesulfonate CF3SO3Na，34mg (0.2mmol) of hexafluoroisopropanol HFIP and 171mg (0.1 mmol/mL) of the electrolyte tetra-n-butylammonium perchlorate. Inserting an electrode (a carbon rod is used as an anode, a platinum sheet is used as a cathode), supplying 5mA with a direct current power supply, and stirring for reaction for 5 hours. After the reaction, the solvent was removed from the reaction mixture by a rotary evaporator, the crude product was extracted with ethyl acetate (10 mL. times.3), the organic layers were combined, washed with saturated NaCl solution (20 mL. times.1) and anhydrous Na2SO4Drying, decompressing and evaporating to dryness, and separating to obtain the target product (Z) -3-amino-2-bromobutyl-2-alkene nitrile with the yield of 62 percent.
Preparation of the desired product (Z) -3-amino-2-bromobut-2-enenitrile obtained in the above example1The H NMR spectrum is shown in fig. 1, identifying data as:1H NMR(500MHz,CDCl3)δ4.95(s,2H),2.19(s,3H).
preparation of the desired product (Z) -3-amino-2-bromobut-2-enenitrile obtained in the above example13The C NMR spectrum is shown in FIG. 2, and the identification data is as follows:13C NMR(126MHz,CDCl3)δ155.0,118.5,57.8,19.4.
the above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. An electrochemical preparation method of (Z) -3-amino-2-bromobut-2-enenitrile is characterized by comprising the following steps:
(1) adding tetra-n-butylammonium bromide and a solvent into a diaphragm-free electrolytic cell, and then adding a sulfur ylide reagent, sodium trifluoromethanesulfonate, an electrolyte and hexafluoroisopropanol;
(2) inserting an electrode into the reaction solution, stirring at room temperature, and electrifying for reaction until the raw materials react completely;
(3) and (Z) -3-amino-2-bromobutyl-2-alkene nitrile is obtained by extracting, concentrating, separating and purifying the reaction liquid.
2. The electrochemical process for preparing (Z) -3-amino-2-bromobut-2-enenitrile as claimed in claim 1, wherein the thioylide reagent in step (1) is 2- (dimethyl (oxo) -sulfenyl) -1-phenylethane-1-one.
3. The electrochemical preparation method of (Z) -3-amino-2-bromobut-2-enenitrile as claimed in claim 1, wherein the molar ratio of tetra-n-butylammonium bromide to thioylide reagent in step (1) is 1: 2.
4. The electrochemical preparation method of (Z) -3-amino-2-bromobut-2-enenitrile as claimed in claim 1, wherein the molar ratio of sodium trifluoromethanesulfonate to tetra-n-butylammonium bromide in step (1) is 3:1-4: 1.
5. The electrochemical production method of (Z) -3-amino-2-bromobut-2-enenitrile as claimed in claim 1, wherein the electrolyte in step (1) is tetra-n-butyl ammonium perchlorate, tetra-n-butyl ammonium tetrafluoroborate or tetra-n-butyl ammonium hexafluorophosphate.
6. The electrochemical preparation method of (Z) -3-amino-2-bromobut-2-enenitrile as claimed in claim 1, characterized in that the solvent in step (1) is acetonitrile.
7. The electrochemical preparation method of (Z) -3-amino-2-bromobut-2-enenitrile as claimed in claim 1, wherein the ratio of the amount of substance of the electrolyte in step (1) to the volume of the solvent is 0.1 mmol/mL.
8. The electrochemical preparation method of (Z) -3-amino-2-bromobut-2-enenitrile as claimed in claim 1, wherein the molar ratio of hexafluoroisopropanol to tetra-n-butylammonium bromide in step (1) is 2:1-3: 1.
9. The electrochemical preparation method of (Z) -3-amino-2-bromobut-2-enenitrile as claimed in claim 1, characterized in that the electrode in step (2) is: a carbon rod anode and a platinum sheet cathode.
10. The electrochemical preparation method of (Z) -3-amino-2-bromobut-2-enenitrile as claimed in any one of claims 1 to 9, characterized in that the current intensity of the electrical reaction in step (2) is 5mA, and the time of the electrical reaction is 4 to 5 h.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN88100844A (en) * | 1987-02-17 | 1988-08-31 | 赫彻斯特股份公司 | Carry out the electrochemical method of halogen atom exchange in the organic compound |
| US4941954A (en) * | 1989-05-08 | 1990-07-17 | E. I. Du Pont De Nemours And Company | Electrochemical preparation of branched unsaturated dinitriles |
| CN1268193A (en) * | 1997-09-05 | 2000-09-27 | 巴斯福股份公司 | Electrochemical reduction of organic compounds |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN88100844A (en) * | 1987-02-17 | 1988-08-31 | 赫彻斯特股份公司 | Carry out the electrochemical method of halogen atom exchange in the organic compound |
| US4941954A (en) * | 1989-05-08 | 1990-07-17 | E. I. Du Pont De Nemours And Company | Electrochemical preparation of branched unsaturated dinitriles |
| CN1268193A (en) * | 1997-09-05 | 2000-09-27 | 巴斯福股份公司 | Electrochemical reduction of organic compounds |
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