CN103214328A - Synthesis method for alpha-bromo-aromatic ketone compounds - Google Patents
Synthesis method for alpha-bromo-aromatic ketone compounds Download PDFInfo
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- CN103214328A CN103214328A CN2013101463025A CN201310146302A CN103214328A CN 103214328 A CN103214328 A CN 103214328A CN 2013101463025 A CN2013101463025 A CN 2013101463025A CN 201310146302 A CN201310146302 A CN 201310146302A CN 103214328 A CN103214328 A CN 103214328A
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- FDTXZYHBRODWDS-UHFFFAOYSA-N COc1ccc(C(C(c(cc2)ccc2[N+]([O-])=O)=O)[Br]=C)cc1 Chemical compound COc1ccc(C(C(c(cc2)ccc2[N+]([O-])=O)=O)[Br]=C)cc1 FDTXZYHBRODWDS-UHFFFAOYSA-N 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P20/582—Recycling of unreacted starting or intermediate materials
Abstract
The invention relates to a synthesis method for alpha-bromo-aromatic ketone compounds, and aims at solving the problems of pollution to environment, no selectivity and low yield of the existing synthesis method for alpha-bromo-aromatic ketone compounds. The specific method comprises the following steps of: adding a bromination reagent and a photoreaction catalyst in aromatic ethylene oxide compounds; reacting in an organic solvent for 6-12 hours at a room temperature under the irradiation of a visible light; filtering and concentrating; and taking the mixed solution of petroleum ether and alpha-bromo-aromatic ketone in a volume ratio of (10-16):1 as an eluent, and performing silica gel column chromatography purification and separation to obtain the alpha-bromo-aromatic ketone compounds, namely, finishing the synthesis method for the alpha-bromo-aromatic ketone compounds. The synthesis method for the alpha-bromo-aromatic ketone compounds disclosed by the invention is applied to the field of chemical industry.
Description
Technical field
The present invention relates to a kind of synthetic method of alpha-brominated aromatic ketone compounds.
Background technology
Alpha-brominated aromatic ketone compounds is the important intermediate of Minute Organic Synthesis chemical such as medicine and agricultural chemicals.Because it has high reaction activity, attracted increasing concern aspect the complicated molecule constructing as the precursor fragment, people also pay attention to the research of its synthetic method more.
The synthetic method of alpha-brominated aromatic ketone compounds is a lot, and wherein most methods is to adopt liquid bromine or hydrogen bromide as bromide reagent the alpha-position of corresponding aromatic ketone to be carried out bromo.Yet, the use of such bromide reagent but is restricted day by day, this is because the safety issue in its toxicity, strong volatility and pungency, the corrodibility to equipment, production and the transportation and produce a large amount of acid waste gas and can produce environment and pollute greatly and destroy, can threaten the harmonious development of human society inevitably, productive rate only is about 50%, and can generate monobromo simultaneously and replace and the dibromo substitution product poor selectivity of reaction.Therefore, use the free of contamination bromide reagent of low toxicity, seek a kind of environmental protection, synthetic method simple to operate and that have an alpha-brominated aromatic ketone compounds of selectivity, high yield conforms with people's demand.
Summary of the invention
The present invention is that the synthetic method that will solve existing alpha-brominated aromatic ketone compounds has pollution, poor selectivity and productive rate to hang down problem to environment, and a kind of synthetic method of alpha-brominated aromatic ketone compounds is provided.
The synthetic method of a kind of alpha-brominated aromatic ketone compounds of the present invention, undertaken by following steps: in the aromatic epoxy ethane compound, add bromide reagent and photoresponse catalyzer, then under radiation of visible light, room temperature reaction 6～12h in organic solvent, filter then and concentration of reaction solution to doing, be (10～16) with volume ratio again: 1 sherwood oil: the mixing solutions of ethyl acetate is as eluent, carrying out purification by silica gel column chromatography separates, obtain alpha-brominated aromatic ketone compounds, promptly finish the synthetic method of alpha-brominated aromatic ketone compounds, wherein bromide reagent is carbon tetrabromide or metal bromide, and the photoresponse catalyzer is the terpyridyl ruthenium chloride; Wherein the mol ratio of aromatic epoxy ethane compound and bromide reagent is 1: (1.1～1.5), the mol ratio of aromatic epoxy ethane compound and photoresponse catalyzer is 1: (0.01～0.05).
The present invention can react at normal temperatures and pressures, and the reaction conditions gentleness need not strict remove water treatment and protection of inert gas, and order of addition(of ingredients) is any, and is simple to operation.Reaction adopts the visible light that cleans, is easy to get as energy derive, and the incandescent light of family expenses, LED lamp and sunlight all can be used as light source, cleanliness without any pollution; The bromide reagent that adopts is the carbon tetrabromide or the metal bromide of low toxicity, and is cheap and easy to get, is easy to feed in raw material, and the cocatalyst Sodium Persulfate cheaply is easy to get and is pollution-free; The photocatalyst consumption is few and can recycling.And reaction substrate of the present invention is applied widely, can utilize the high yield of different aromatic epoxy ethane class substrate realization responses, for example alkyl, ketone group, ester group and aromatic group etc.Productive rate of the present invention and selectivity are all higher, and the partial reaction yield can be up to more than 90%, and generates single bromination product, and the product that no dibromo replaces generates; The entire reaction safety and environmental protection, cost is low, and the economic benefit height belongs to green chemistry process.
Embodiment
Embodiment one: the synthetic method of a kind of alpha-brominated aromatic ketone compounds of present embodiment, undertaken by following steps: in the aromatic epoxy ethane compound, add bromide reagent and photoresponse catalyzer, then under radiation of visible light, room temperature reaction 6～12h in organic solvent, filter then and concentration of reaction solution to doing, be (10～16) with volume ratio again: 1 sherwood oil: the mixing solutions of ethyl acetate is as eluent, carrying out purification by silica gel column chromatography separates, obtain alpha-brominated aromatic ketone compounds, promptly finish the synthetic method of alpha-brominated aromatic ketone compounds, wherein bromide reagent is carbon tetrabromide or metal bromide, and the photoresponse catalyzer is the terpyridyl ruthenium chloride; Wherein the mol ratio of aromatic epoxy ethane compound and bromide reagent is 1: (1.1～1.5), the mol ratio of aromatic epoxy ethane compound and photoresponse catalyzer is 1: (0.01～0.05).
The reaction formula of present embodiment is:
Present embodiment is suitable for all aromatic epoxy ethane compounds.
Present embodiment can be reacted at normal temperatures and pressures, and the reaction conditions gentleness need not strict remove water treatment and protection of inert gas, and order of addition(of ingredients) is any, and is simple to operation.Reaction adopts the visible light that cleans, is easy to get as energy derive, and the incandescent light of family expenses, LED lamp and sunlight all can be used as light source, cleanliness without any pollution; The bromide reagent that adopts is the carbon tetrabromide or the metal bromide of low toxicity, and is cheap and easy to get, is easy to feed in raw material, and the cocatalyst Sodium Persulfate cheaply is easy to get and is pollution-free; The photocatalyst consumption is few and can recycling.And the reaction substrate of present embodiment is applied widely, can utilize the high yield of different aromatic epoxy ethane class substrate realization responses, for example alkyl, ketone group, ester group and aromatic group etc.The productive rate of present embodiment and selectivity are all higher, and the partial reaction yield can be up to more than 90%, and generates single bromination product, and the product that no dibromo replaces generates; The entire reaction safety and environmental protection, cost is low, and the economic benefit height belongs to green chemistry process.
Embodiment two: present embodiment and embodiment one are different is that bromide reagent is when being metal bromide, add the cocatalyst Sodium Persulfate in the aromatic epoxy ethane compound, wherein the mol ratio of aromatic epoxy ethane compound and Sodium Persulfate is 1: (1～2).Other steps are identical with embodiment one with parameter.
Embodiment three: present embodiment is different with embodiment one or two is that the mol ratio of aromatic epoxy ethane compound and bromide reagent is 1: (1.1～1.2).Other steps are identical with embodiment one or two with parameter.
Embodiment four: present embodiment is different with one of embodiment one to three is that the mol ratio of aromatic epoxy ethane compound and photoresponse catalyzer is 1: (0.02～0.04).Other steps are identical with one of embodiment one to three with parameter.
Embodiment five: what present embodiment was different with one of embodiment one to four is that organic solvent is acetonitrile, methyl alcohol or N, and dinethylformamide, consumption are the organic solvent that every mmole aromatic epoxy ethane compound uses the 5-10 milliliter.Other steps are identical with one of embodiment one to four with parameter.
Embodiment six: what present embodiment was different with one of embodiment one to five is that visible light is incandescent light, LED lamp or sunlight.Other steps are identical with one of embodiment one to five with parameter.
By following verification experimental verification beneficial effect of the present invention:
Test 1, a kind of synthetic method of alpha-brominated aromatic ketone compounds, undertaken by following steps: in reaction flask, add 45.3mg2-(4-p-methoxy-phenyl)-3-phenyl ethylene oxide, 99.5mg carbon tetrabromide and 7.5mg terpyridyl ruthenium chloride catalyzer, drawing the 2mL acetonitrile with syringe then joins in the reaction flask, the rubber plug that is inserted with syringe needle beyond the Great Wall is placed under the radiation of visible light, room temperature reaction 7h, filter then and concentration of reaction solution to doing, be 10: 1 sherwood oil again with volume ratio: the mixing solutions of ethyl acetate is as eluent, carrying out purification by silica gel column chromatography separates, obtain 2-bromo-2-(4-p-methoxy-phenyl)-1-methyl phenyl ketone, promptly finish the synthetic method of alpha-brominated aromatic ketone compounds.Wherein the structural formula of 2-bromo-2-(4-p-methoxy-phenyl)-1-methyl phenyl ketone is:
This test synthetic 2-bromo-2-(4-p-methoxy-phenyl)-1-methyl phenyl ketone is a light yellow solid, and productive rate is 92%, and its nuclear magnetic data is:
1H NMR (400MHz, CDCl
3): δ 7.98 (d, J=7.8Hz, 2H), 7.56 (t, J=7.4Hz, 1H), 7.49-7.42 (m, 4H), 6.89 (d, J=8.7Hz, 2H), 6.40 (s, 1H), 3.80 (s, 3H).
13C NMR (100MHz, CDCl
3): δ 191.2,160.3, and 134.3,133.7,130.6,129.2,128.9,127.9,114.6,55.4,51.4.
Test 2, a kind of synthetic method of alpha-brominated aromatic ketone compounds, undertaken by following steps: in reaction flask, add 32.8mg2-(4-p-methoxy-phenyl)-3-methyl oxirane, the 26mg lithiumbromide, 90mg Sodium Persulfate and 7.5mg terpyridyl ruthenium chloride catalyzer, drawing the 2mL acetonitrile with syringe then joins in the reaction flask, the rubber plug that is inserted with syringe needle beyond the Great Wall is placed under the radiation of visible light, room temperature reaction 8h, filter then and concentration of reaction solution to doing, be 16: 1 sherwood oil again with volume ratio: the mixing solutions of ethyl acetate is as eluent, carrying out purification by silica gel column chromatography separates, obtain 1-bromo-1-(4-p-methoxy-phenyl)-2-acetone, promptly finish the synthetic method of alpha-brominated aromatic ketone compounds, wherein the structural formula of 1-bromo-1-(4-p-methoxy-phenyl)-2-acetone is:
This test synthetic 1-bromo-1-(4-p-methoxy-phenyl)-2-acetone is white solid, and productive rate is 88%, and its nuclear magnetic data is: and 1HNMR (400MHz, CDCl3): δ 7.35 (d, J=8.7Hz, 2H), 6.89 (d, J=8.7Hz, 2H), 5.43 (s, 1H), 3.80 (s, 3H), 2.29 (s, 3H) .13C NMR (100MHz, CDCl3): δ 199.3,160.3,130.2,127.2,114.6,56.4,55.5,26.4.
Test 3, a kind of synthetic method of alpha-brominated aromatic ketone compounds, undertaken by following steps: in reaction flask, add 44.4mg3-(4-p-methoxy-phenyl) oxyethane-2-carboxylic acid, ethyl ester, 99.5mg carbon tetrabromide and 7.5mg terpyridyl ruthenium chloride catalyzer, drawing the 2mL acetonitrile with syringe then joins in the reaction flask, the rubber plug that is inserted with syringe needle beyond the Great Wall is placed under the radiation of visible light, room temperature reaction 9h, filter then and concentration of reaction solution to doing, be 16: 1 sherwood oil again with volume ratio: the mixing solutions of ethyl acetate is as eluent, carrying out purification by silica gel column chromatography separates, obtain 3-bromo-3-(4-p-methoxy-phenyl)-Pyruvic Acid Ethyl ester, promptly finish the synthetic method of alpha-brominated aromatic ketone compounds, wherein the structural formula of 3-bromo-3-(4-p-methoxy-phenyl)-Pyruvic Acid Ethyl ester is:
This test synthetic 3-bromo-3-(4-p-methoxy-phenyl)-Pyruvic Acid Ethyl ester is a weak yellow liquid, and productive rate is 67%, and its nuclear magnetic data is: 1HNMR (400MHz, CDCl3): δ 7.39 (d, J=8.7Hz, 2H), 6.90 (d, J=8.7Hz, 2H), 6.22 (s, 1H), 4.32 (qd, J=7.2,3.7Hz, 2H), 3.81 (s, 3H), 1.33 (t, J=7.2Hz, 3H) .13C NMR (100MHz, CDCl3): δ 184.0,160.7,160.3,131.2,125.0,114.6,63.3,55.5,50.1,14.0.
Test 4, a kind of synthetic method of alpha-brominated aromatic ketone compounds, undertaken by following steps: in reaction flask, add 54.2mg2-(4-p-methoxy-phenyl)-3-(4-nitrophenyl) oxyethane, the 26mg lithiumbromide, 90mg Sodium Persulfate and 7.5mg terpyridyl ruthenium chloride catalyzer, drawing the 2mL acetonitrile with syringe then joins in the reaction flask, the rubber plug that is inserted with syringe needle beyond the Great Wall is placed under the radiation of visible light, room temperature reaction 8h, filter then and concentration of reaction solution to doing, be 10: 1 sherwood oil again with volume ratio: the mixing solutions of ethyl acetate is as eluent, carrying out purification by silica gel column chromatography separates, obtain 2-bromo-2-(4-p-methoxy-phenyl)-1-(4-nitrophenyl) ethyl ketone, promptly finish the synthetic method of alpha-brominated aromatic ketone compounds, wherein the structural formula of 2-bromo-2-(4-p-methoxy-phenyl)-1-(4-nitrophenyl) ethyl ketone is:
This test synthetic 2-bromo-2-(4-p-methoxy-phenyl)-1-(4-nitrophenyl) ethyl ketone is a weak yellow liquid, and productive rate is 72%, and its nuclear magnetic data is: 1HNMR (400MHz, CDCl3): δ 8.27 (d, J=8.7Hz, 2H), 8.12 (d, J=8.7Hz, 2H), 7.44 (d, J=8.6Hz, 2H), 6.90 (d, J=8.6Hz, 2H), 6.33 (s, 1H), 3.80 (s, 3H) .13CNMR (100MHz, CDCl3): δ 189.8,160.6,150.5,139.1,130.7,130.3,126.7,124.0,114.8,55.5,51.1.
Test 5, a kind of synthetic method of alpha-brominated aromatic ketone compounds, undertaken by following steps: in reaction flask, add 61.0mg2-(4-bromo phenyl)-3-(4-p-methoxy-phenyl) oxyethane, 99.5mg carbon tetrabromide and 7.5mg terpyridyl ruthenium chloride catalyzer, drawing the 2mL acetonitrile with syringe then joins in the reaction flask, the rubber plug that is inserted with syringe needle beyond the Great Wall is placed under the radiation of visible light, room temperature reaction 10h, filter then and concentration of reaction solution to doing, be 12: 1 sherwood oil again with volume ratio: the mixing solutions of ethyl acetate is as eluent, carrying out purification by silica gel column chromatography separates, obtain 2-bromo-1-(4-bromo phenyl)-2-(4-p-methoxy-phenyl) ethyl ketone, promptly finish the synthetic method of alpha-brominated aromatic ketone compounds, wherein the structural formula of 2-bromo-1-(4-bromo phenyl)-2-(4-p-methoxy-phenyl) ethyl ketone is:
This test synthetic 2-bromo-1-(4-bromo phenyl)-2-(4-p-methoxy-phenyl) ethyl ketone is a faint yellow solid, and productive rate is 86%, and its nuclear magnetic data is:
1H NMR (400MHz, CDCl
3): δ 7.83 (d, J=8.6Hz, 2H), 7.56 (d, J=8.6Hz, 2H), 7.43 (d, J=8.7Hz, 2H), 6.88 (d, J=8.7Hz, 2H), 6.32 (s, 1H), 3.78 (s, 3H).
13CNMR (100MHz, CDCl
3): δ 190.2,160.4,133.0,132.2,130.7,130.6,129.0,127.5,114.6,55.4,51.2.
Test 6, a kind of synthetic method of alpha-brominated aromatic ketone compounds, undertaken by following steps: in reaction flask, add 72.1mg (2-benzyloxy phenyl) (3-(4-p-methoxy-phenyl) oxyethane-2-yl) ketone, the 26mg lithiumbromide, 90mg Sodium Persulfate and 7.5mg terpyridyl ruthenium chloride catalyzer, add then with syringe and draw 2mL methyl alcohol in reaction flask, the rubber plug that is inserted with syringe needle beyond the Great Wall is placed under the radiation of visible light, room temperature reaction 11h, filter then and concentration of reaction solution to doing, be 16: 1 sherwood oil again with volume ratio: the mixing solutions of ethyl acetate is as eluent, carrying out purification by silica gel column chromatography separates, obtain 3-bromo-1-(2-benzyloxy phenyl)-3-(4-p-methoxy-phenyl) propane-1, the 2-diketone, promptly finish the synthetic method of alpha-brominated aromatic ketone compounds, 3-bromo-1-(2-benzyloxy phenyl)-3-(4-p-methoxy-phenyl) propane-1 wherein, the structural formula of 2-diketone is:
This test synthetic 3-bromo-1-(2-benzyloxy phenyl)-3-(4-p-methoxy-phenyl) propane-1, the 2-diketone is a weak yellow liquid, and productive rate is 68%, and its nuclear magnetic data is: 1H NMR (400MHz, CDCl3): δ 7.89 (d, J=7.8Hz, 1H), 7.55 (t, J=7.8Hz, 1H), and 7.48-7.39 (m, 5H), 7.19 (d, J=8.6Hz, 2H), 7.08 (t, J=7.5Hz, 1H), 7.01 (d, J=8.5Hz, 1H), 6.79 (d, J=8.6Hz, 2H), 5.72 (s, 1H), 5.14 (d, J=2.7Hz, 2H), 3.77 (s, 3H) .13CNMR (100MHz, CDCl3): δ 193.0,192.5,1602,159.4,136.5,135.3,131.1,129.0,128.7,128.3,127.1,122.9,121.6,114.3,113.3,71.4,55.4,51.3.
Test 7, a kind of synthetic method of alpha-brominated aromatic ketone compounds, undertaken by following steps: in 57.7mg (4-chloro phenyl) (3-(4-p-methoxy-phenyl) oxyethane-2-yl) ketone, add the 26mg lithiumbromide, 90mg Sodium Persulfate and 7.5mg terpyridyl ruthenium chloride catalyzer, draw 2mLN with syringe then, dinethylformamide joins in the reaction flask, the rubber plug that is inserted with syringe needle beyond the Great Wall is placed under the radiation of visible light, room temperature reaction 10h, filter then and concentration of reaction solution to doing, be 10: 1 sherwood oil again with volume ratio: the mixing solutions of ethyl acetate is as eluent, carrying out purification by silica gel column chromatography separates, obtain 3-bromo-1-(4-chloro phenyl)-3-(4-p-methoxy-phenyl) propane-1, the 2-diketone, promptly finish the synthetic method of alpha-brominated aromatic ketone compounds, 3-bromo-1-(4-chloro phenyl)-3-(4-p-methoxy-phenyl) propane-1 wherein, the structural formula of 2-diketone is:
This test synthetic 3-bromo-1-(4-chloro phenyl)-3-(4-p-methoxy-phenyl) propane-1, the 2-diketone is a faint yellow solid, productive rate is 75%, its nuclear magnetic data is: and 1H NMR (400MHz, CDCl3): δ 7.97 (d, J=8.5Hz, 2H), 7.48 (d, J=8.2Hz, 2H), 6.91 (d, J=9.5Hz, 2H), 6.37 (s, 1H), 3.82 (s, 3H) .13C NMR (100MHz, CDCl3): δ 189.9,189.4,160.8,141.9,131.8,131.4,130.7,129.5,124.8,114.6,55.5,49.8.
By test 1～test 7 as can be known, this test reaction conditions gentleness need not strict remove water treatment and protection of inert gas, and order of addition(of ingredients) is any, and is simple to operation.Reaction adopts the visible light that cleans, is easy to get as energy derive, and the incandescent light of family expenses, LED lamp and sunlight all can be used as light source, cleanliness without any pollution; The bromide reagent that adopts is the carbon tetrabromide or the metal bromide of low toxicity, and is cheap and easy to get, is easy to feed in raw material, and the cocatalyst Sodium Persulfate cheaply is easy to get and is pollution-free; The photocatalyst consumption is few and can recycling.And the reaction substrate of this test is applied widely, can utilize the high yield of different aromatic epoxy ethane class substrate realization responses, for example alkyl, ketone group, ester group and aromatic group etc.Productive rate of this test and selectivity are all higher, and the partial reaction yield can be up to more than 90%, and generates single bromination product, and the product that no dibromo replaces generates; The entire reaction safety and environmental protection, cost is low, and the economic benefit height belongs to green chemistry process.
Claims (6)
1. the synthetic method of an alpha-brominated aromatic ketone compounds, the synthetic method that it is characterized in that alpha-brominated aromatic ketone compounds is undertaken by following steps: add bromide reagent and photoresponse catalyzer in the aromatic epoxy ethane compound, then under radiation of visible light, room temperature reaction 6～12h in organic solvent, filter then and concentration of reaction solution to doing, again with mixing solutions as eluent, carrying out purification by silica gel column chromatography separates, obtain alpha-brominated aromatic ketone compounds, promptly finish the synthetic method of alpha-brominated aromatic ketone compounds, wherein bromide reagent is carbon tetrabromide or metal bromide, and the photoresponse catalyzer is the terpyridyl ruthenium chloride; Mixing solutions is by sherwood oil: ethyl acetate is (10～16) by volume: 1 mixed forms; Wherein the mol ratio of aromatic epoxy ethane compound and bromide reagent is 1: (1.1～1.5), the mol ratio of aromatic epoxy ethane compound and photoresponse catalyzer is 1: (0.01～0.05).
2. the synthetic method of a kind of alpha-brominated aromatic ketone compounds according to claim 1, it is characterized in that bromide reagent is a metal bromide, add the cocatalyst Sodium Persulfate in the aromatic epoxy ethane compound, wherein the mol ratio of aromatic epoxy ethane compound and Sodium Persulfate is 1: (1～2).
3. the synthetic method of a kind of alpha-brominated aromatic ketone compounds according to claim 1, the mol ratio that it is characterized in that aromatic epoxy ethane compound and bromide reagent is 1: (1.1～1.2).
4. the synthetic method of a kind of alpha-brominated aromatic ketone compounds according to claim 1, the mol ratio that it is characterized in that aromatic epoxy ethane compound and photoresponse catalyzer is 1: (0.02～0.04).
5. the synthetic method of a kind of alpha-brominated aromatic ketone compounds according to claim 1, it is characterized in that organic solvent is acetonitrile, methyl alcohol or N, dinethylformamide, consumption are the organic solvent that every mmole aromatic epoxy ethane compound uses the 5-10 milliliter.
6. the synthetic method of a kind of alpha-brominated aromatic ketone compounds according to claim 1 is characterized in that visible light is incandescent light, LED lamp or sunlight.
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| CN106916146A (en) * | 2017-04-28 | 2017-07-04 | 南京工业大学 | The method that a kind of oxa- cyclics of visible light catalytic are coupled with quinoline dehydrogenation |
| CN108774128A (en) * | 2018-07-16 | 2018-11-09 | 浙江工业大学 | A kind of α preparing carbonyl substitution, the synthetic method of beta-unsaturated carboxylic acid ester |
| CN111675650A (en) * | 2020-05-26 | 2020-09-18 | 哈尔滨工业大学(深圳)(哈尔滨工业大学深圳科技创新研究院) | Preparation method of aromatic vinyl bromide derivative |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105463500A (en) * | 2015-11-19 | 2016-04-06 | 上海师范大学 | Method for preparing aromatic aldehyde/ketone compound based on photoelectrocatalysis |
| CN106916146A (en) * | 2017-04-28 | 2017-07-04 | 南京工业大学 | The method that a kind of oxa- cyclics of visible light catalytic are coupled with quinoline dehydrogenation |
| CN108774128A (en) * | 2018-07-16 | 2018-11-09 | 浙江工业大学 | A kind of α preparing carbonyl substitution, the synthetic method of beta-unsaturated carboxylic acid ester |
| CN111675650A (en) * | 2020-05-26 | 2020-09-18 | 哈尔滨工业大学(深圳)(哈尔滨工业大学深圳科技创新研究院) | Preparation method of aromatic vinyl bromide derivative |
| CN111675650B (en) * | 2020-05-26 | 2021-09-03 | 哈尔滨工业大学(深圳)(哈尔滨工业大学深圳科技创新研究院) | Preparation method of aromatic vinyl bromide derivative |
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