CN113930793A - Method for preparing 3-methyl-5-bromomethylpyridine bromate by using electrochemical microchannel reaction device - Google Patents
Method for preparing 3-methyl-5-bromomethylpyridine bromate by using electrochemical microchannel reaction device Download PDFInfo
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- CN113930793A CN113930793A CN202111414867.8A CN202111414867A CN113930793A CN 113930793 A CN113930793 A CN 113930793A CN 202111414867 A CN202111414867 A CN 202111414867A CN 113930793 A CN113930793 A CN 113930793A
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 21
- ASESODVAUAPQQF-UHFFFAOYSA-N Br(=O)(=O)O.CC=1C=C(C=NC1)CBr Chemical compound Br(=O)(=O)O.CC=1C=C(C=NC1)CBr ASESODVAUAPQQF-UHFFFAOYSA-N 0.000 title claims abstract description 17
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000012456 homogeneous solution Substances 0.000 claims abstract description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003792 electrolyte Substances 0.000 claims abstract description 5
- 239000012046 mixed solvent Substances 0.000 claims abstract description 5
- 238000005086 pumping Methods 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- -1 tetrabutylammonium tetrafluoroborate Chemical compound 0.000 claims description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910002804 graphite Inorganic materials 0.000 claims description 5
- 239000010439 graphite Substances 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Chemical group 0.000 claims description 2
- 239000001257 hydrogen Chemical group 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- 239000011591 potassium Chemical group 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract description 4
- CZALOULBSKSWNH-UHFFFAOYSA-N 3-(bromomethyl)-5-methylpyridine Chemical compound CC1=CN=CC(CBr)=C1 CZALOULBSKSWNH-UHFFFAOYSA-N 0.000 abstract description 2
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- JYBLCDXVHQWMSU-WLHGVMLRSA-N (e)-but-2-enedioic acid;8-chloro-11-[1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene]-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridine Chemical compound OC(=O)\C=C\C(O)=O.CC1=CN=CC(CN2CCC(CC2)=C2C3=NC=CC=C3CCC3=CC(Cl)=CC=C32)=C1 JYBLCDXVHQWMSU-WLHGVMLRSA-N 0.000 description 2
- HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 2
- 108010003541 Platelet Activating Factor Proteins 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CKEAZZPEMCPDPI-UHFFFAOYSA-N 3-(bromomethyl)-5-methylpyridine;hydrobromide Chemical compound Br.CC1=CN=CC(CBr)=C1 CKEAZZPEMCPDPI-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/09—Nitrogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/05—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/11—Halogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
Abstract
The invention discloses a method for preparing 3-methyl-5-bromomethylpyridine bromate by using an electrochemical microchannel reaction device, which comprises the following steps: dissolving 3, 5-dimethylpyridine, bromine salt and electrolyte in a mixed solvent to obtain a homogeneous solution, and pumping the homogeneous solution into a microchannel reaction device provided with electrodes for electrolytic reaction to obtain the catalyst. Compared with the prior art, the method greatly reduces the generation of byproducts and obviously improves the yield of the 3-methyl-5-bromomethylpyridine. Meanwhile, the raw materials are more green, environment-friendly and economical, and the method is more favorable for industrial large-scale production.
Description
Technical Field
The invention belongs to the technical field of preparation of 3-methyl-5-bromomethylpyridine bromate, and particularly relates to a method for preparing 3-methyl-5-bromomethylpyridine bromate by using an electrochemical microchannel reaction device.
Background
Rupatadine fumarate was successfully developed by Uriach pharmaceutical corporation of Spain and was first marketed in Spain in 2003. It is a new generation of tricyclic antihistamine medicine, and has dual effects of antihistaminic and antagonistic Platelet Activating Factor (PAF). Is often used for resisting allergy clinically, and has certain effect on allergic diseases. 3-methyl-5-bromomethylpyridine is an important intermediate of rupatadine fumarate.
The traditional preparation process of the intermediate has two types, wherein the route I adopts NBS or NCS free radical halogenation reaction, the process has the problems of low effective conversion rate, more polyhalogenated byproducts and severe safety risk caused by the reaction in the free radical reaction. The step in the route II is longer, and the problem of higher price of the starting material exists, so that the method is not beneficial to industrial production.
Disclosure of Invention
The purpose of the invention is as follows: the invention provides a method for preparing 3-methyl-5-bromomethylpyridine bromate by using an electrochemical microchannel reaction device, which can solve the problems of more byproducts or complicated steps, expensive starting materials and the like in the traditional preparation process, can obviously improve the reaction yield, and is suitable for industrial production.
The technical scheme is as follows: in order to achieve the purpose, the invention adopts the following technical scheme:
a method for preparing 3-methyl-5-bromomethylpyridine bromate by using an electrochemical microchannel reaction device comprises the following steps:
dissolving 3, 5-dimethylpyridine, bromine salt and electrolyte in a mixed solvent to obtain a homogeneous solution, and pumping the homogeneous solution into a microchannel reaction device provided with electrodes for electrolytic reaction to obtain the product;
wherein R is sodium, potassium, hydrogen, etc.
Preferably, the bromine salt is selected from one of sodium bromide, potassium bromide, hydrogen bromide and ammonium bromide, and sodium bromide is more preferred.
Preferably, the electrolyte is selected from one or more of tetrabutylammonium tetrafluoroborate, tetrabutylammonium acetate and tetrabutylammonium hexafluorophosphate, and further preferably tetrabutylammonium tetrafluoroborate.
Preferably, the concentration of the 3, 5-lutidine in the homogeneous solution is 0.02-0.05mol/L, and more preferably 0.0375 mol/L; the concentration of the bromine salt is 0.035 to 0.055mol/L, and more preferably 0.045 mol/L.
Preferably, the mixed solvent is selected from one or more of acetonitrile, dimethyl sulfoxide, N-dimethylformamide, 1, 2-dichloroethane, trifluoroethanol, ethanol and methanol in different proportions, and more preferably 1, 2-dichloroethane: acetonitrile 5: 3.
preferably, the electrode comprises an anode sheet and a cathode sheet, the anode sheet is a graphite carbon electrode or a platinum sheet electrode, and the graphite carbon electrode is further preferred; the cathode sheet is a graphite carbon electrode or a platinum sheet electrode, and a platinum sheet electrode is further preferred.
Preferably, the flow rate of the homogeneous solution pumped into the microchannel reaction device is 0.10-0.55mL/min, and more preferably 0.15 mL/min; the current of the electrolytic reaction is 5 to 20mA, more preferably 10 mA; the reaction temperature is 0 to 30 ℃ and more preferably 25 ℃.
Preferably, the microchannel reaction device comprises a feeding pump, a microreactor, a cathode sheet, an anode sheet and a receiver; the feeding pump, the micro-reactor and the receiver are connected in series, and a cathode sheet and an anode sheet are respectively arranged on two sides of the micro-reactor.
Wherein, the connection is a pipeline connection, and the pipeline material is polytetrafluoroethylene.
Preferably, in the microchannel reaction device, the reaction volume of the microreactor is 0.5-1.5mL, and more preferably 1.25 mL.
After the above reaction was complete, the microreactor effluent was collected, hydrobromic acid (1mL) was added, the mixture was concentrated under reduced pressure, and the residue was taken up in tetrahydrofuran: ethanol ═ 1: 1(20mL) is stirred for 30min, white solid is separated out, and the pure product of the 3-methyl-5-bromomethylpyridine bromate is obtained after filtration and drying.
Has the advantages that: compared with the prior art, the method greatly reduces the generation of polyhalogenated byproducts and obviously improves the yield of the 3-methyl-5-bromomethylpyridine hydrobromide. Meanwhile, the raw materials are safer, more environment-friendly and more economical to select, and the method is suitable for industrial large-scale production.
Detailed Description
The following examples are given to further illustrate the embodiments of the present invention. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The reactions in the following examples were all carried out in an undivided electrolytic cell, with electrodes inserted into the reaction solution.
Example 1
Weighing 0.3mmol (0.0321g) of 3, 5-dimethylpyridine, 0.36mmol (0.0370g) of sodium bromide, 0.1mmol (0.0329g) of tetrabutylammonium tetrafluoroborate, 5mL of 1, 2-dichloroethane and 3mL of acetonitrile, preparing a homogeneous solution, adding the homogeneous solution into an injection pump, injecting the injection pump into a microreactor at the flow rate of 0.15mL/min for reaction, wherein the reaction volume of the microreactor is 1.25mL, the temperature of the microreactor is 25 ℃, and the reaction current is 10 mA; after the above reaction was complete, the microreactor effluent was collected, hydrobromic acid (1mL) was added, the mixture was concentrated under reduced pressure, and the residue was taken up in tetrahydrofuran: ethanol ═ 1: 1(20mL) is stirred for 30min, white solid is separated out, and the target product is obtained after filtration and pumping-out, wherein the yield is 84%.
1H NMR(400MHz,DMSO-d6)δ8.92(t,J＝1.7Hz,1H),8.73-7.71(m,1H),7.94– 7.91(m,1H),4.64(s,2H),2.51-2.46(m,3H)；13C NMR(100MHz,DMSO-d6)δ138.53, 138.07,137.68,137.64,136.23,30.28,18.01.
Example 2
Weighing 0.3mmol (0.0321g) of 3, 5-dimethylpyridine, 0.36mmol (0.0370g) of sodium bromide, 0.1mmol (0.0329g) of tetrabutylammonium tetrafluoroborate, 7.5mL of 1, 2-dichloroethane and 4.5mL of acetonitrile, preparing a homogeneous solution, adding the homogeneous solution into an injection pump, injecting the injection pump into a microreactor at the flow rate of 0.15mL/min for reaction, wherein the reaction volume of the microreactor is 1.25mL, the temperature of the microreactor is 25 ℃, and the reaction current is 10 mA; after the above reaction was complete, the microreactor effluent was collected, hydrobromic acid (1mL) was added, the mixture was concentrated under reduced pressure, and the residue was taken up in tetrahydrofuran: ethanol ═ 1: 1(20mL) is stirred for 30min, white solid is separated out, and the target product is obtained after filtration and pumping-out, wherein the yield is 73%.
Example 3
Weighing 0.3mmol (0.0321g) of 3, 5-dimethylpyridine, 0.36mmol (0.0370g) of sodium bromide, 0.1mmol (0.0329g) of tetrabutylammonium tetrafluoroborate, 5mL of 1, 2-dichloroethane and 3mL of acetonitrile, preparing a homogeneous solution, adding the homogeneous solution into an injection pump, injecting the injection pump into a microreactor at the flow rate of 0.3mL/min for reaction, wherein the reaction volume of the microreactor is 1.25mL, the temperature of the microreactor is 25 ℃, and the reaction current is 10 mA; after the above reaction was complete, the microreactor effluent was collected, hydrobromic acid (1mL) was added, the mixture was concentrated under reduced pressure, and the residue was taken up in tetrahydrofuran: ethanol ═ 1: 1(20mL) is stirred for 30min, white solid is separated out, and the target product is obtained after filtration and pumping-out, wherein the yield is 61%.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (9)
1. A method for preparing 3-methyl-5-bromomethylpyridine bromate by using an electrochemical microchannel reaction device is characterized by comprising the following steps:
dissolving 3, 5-dimethylpyridine, bromine salt and electrolyte in a mixed solvent to obtain a homogeneous solution, and pumping the homogeneous solution into a microchannel reaction device provided with electrodes for electrolytic reaction to obtain the product;
wherein R is sodium, potassium or hydrogen.
2. The method for preparing 3-methyl-5-bromomethylpyridine bromate using the electrochemical microchannel reaction device according to claim 1, wherein the bromine salt is selected from one of sodium bromide, potassium bromide, hydrogen bromide and ammonium bromide.
3. The method for preparing 3-methyl-5-bromomethylpyridine bromate by using the electrochemical microchannel reaction device according to claim 1, wherein the electrolyte is one or more selected from tetrabutylammonium tetrafluoroborate, tetrabutylammonium acetate and tetrabutylammonium hexafluorophosphate.
4. The method for preparing 3-methyl-5-bromomethylpyridine bromate by using the electrochemical microchannel reaction device according to claim 1, wherein the concentration of 3, 5-dimethylpyridine in the homogeneous solution is 0.02-0.05mol/L, and the concentration of bromine salt is 0.035-0.055 mol/L.
5. The method for preparing 3-methyl-5-bromomethylpyridine bromate by using the electrochemical microchannel reaction device according to claim 1, wherein the mixed solvent is one or more of acetonitrile, dimethyl sulfoxide, N-dimethylformamide, 1, 2-dichloroethane, trifluoroethanol, ethanol and methanol in different proportions.
6. The method for preparing 3-methyl-5-bromomethylpyridine bromate using an electrochemical microchannel reaction device according to claim 1, wherein the electrodes comprise an anode sheet and a cathode sheet, the anode sheet is a graphite carbon electrode or a platinum sheet electrode, and the cathode sheet is a graphite carbon electrode or a platinum sheet electrode.
7. The method for preparing 3-methyl-5-bromomethylpyridine bromate using an electrochemical microchannel reaction device according to claim 1, wherein the flow rate of the homogeneous solution pumped into the microchannel reaction device is 0.10 to 0.55mL/min, the current of the electrolytic reaction is 5 to 20mA, and the reaction temperature is 0 to 30 ℃.
8. The method for preparing 3-methyl-5-bromomethylpyridine bromate using an electrochemical microchannel reaction device according to claim 1, wherein the microchannel reaction device comprises a feed pump, a microreactor, a cathode sheet, an anode sheet and a receiver; the feeding pump, the micro-reactor and the receiver are connected in series, and a cathode sheet and an anode sheet are respectively arranged on two sides of the micro-reactor.
9. The method for preparing 3-methyl-5-bromomethylpyridine bromate using the electrochemical microchannel reaction device according to claim 1, wherein the reaction volume of the microreactor in the microchannel reaction device is 0.5-1.5 mL.
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| CN115074761A (en) * | 2022-07-13 | 2022-09-20 | 南京大学 | Method for synthesizing adiponitrile by electrochemical reduction based on microreactor |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103959533A (en) * | 2011-09-22 | 2014-07-30 | 溴化合物有限公司 | Additives for hydrogen/bromine cells |
| CN104163786A (en) * | 2014-06-10 | 2014-11-26 | 上海应用技术学院 | Method for preparing 5-methyl-3-bromomethylpyridine hydrobromide |
| CN105026371A (en) * | 2013-02-07 | 2015-11-04 | 溴化合物有限公司 | Processes for preparing l-alkyl-3-alkyl-pyridinium bromide and uses thereof as additives in electrochemical cells |
| CN105399661A (en) * | 2015-12-14 | 2016-03-16 | 华东师范大学 | Preparation method for 2,6-dibromo methyl pyridine |
| CN109020912A (en) * | 2018-07-26 | 2018-12-18 | 南京昊绿生物科技有限公司 | The synthesis technology of C-Fos/AP-1 inhibitor |
| CN112144074A (en) * | 2020-10-26 | 2020-12-29 | 南京先进生物材料与过程装备研究院有限公司 | Method for preparing dibit bromoindole by using electrochemical microchannel device |
| CN113235116A (en) * | 2021-05-12 | 2021-08-10 | 齐鲁工业大学 | Electrochemical synthesis method of bromopyridine derivative |
-
2021
- 2021-11-25 CN CN202111414867.8A patent/CN113930793B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103959533A (en) * | 2011-09-22 | 2014-07-30 | 溴化合物有限公司 | Additives for hydrogen/bromine cells |
| CN105026371A (en) * | 2013-02-07 | 2015-11-04 | 溴化合物有限公司 | Processes for preparing l-alkyl-3-alkyl-pyridinium bromide and uses thereof as additives in electrochemical cells |
| CN104163786A (en) * | 2014-06-10 | 2014-11-26 | 上海应用技术学院 | Method for preparing 5-methyl-3-bromomethylpyridine hydrobromide |
| CN105399661A (en) * | 2015-12-14 | 2016-03-16 | 华东师范大学 | Preparation method for 2,6-dibromo methyl pyridine |
| CN109020912A (en) * | 2018-07-26 | 2018-12-18 | 南京昊绿生物科技有限公司 | The synthesis technology of C-Fos/AP-1 inhibitor |
| CN112144074A (en) * | 2020-10-26 | 2020-12-29 | 南京先进生物材料与过程装备研究院有限公司 | Method for preparing dibit bromoindole by using electrochemical microchannel device |
| CN113235116A (en) * | 2021-05-12 | 2021-08-10 | 齐鲁工业大学 | Electrochemical synthesis method of bromopyridine derivative |
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| CN115074761A (en) * | 2022-07-13 | 2022-09-20 | 南京大学 | Method for synthesizing adiponitrile by electrochemical reduction based on microreactor |
| CN115074761B (en) * | 2022-07-13 | 2023-12-26 | 南京大学 | Method for synthesizing adiponitrile by electrochemical reduction based on microreactor |
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