CN109608341A - A kind of aryl aniline compound and preparation method thereof - Google Patents
A kind of aryl aniline compound and preparation method thereof Download PDFInfo
- Publication number
- CN109608341A CN109608341A CN201811624099.7A CN201811624099A CN109608341A CN 109608341 A CN109608341 A CN 109608341A CN 201811624099 A CN201811624099 A CN 201811624099A CN 109608341 A CN109608341 A CN 109608341A
- Authority
- CN
- China
- Prior art keywords
- added
- container
- aryl
- aniline compound
- added dropwise
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/46—Aniline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/02—Magnesium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a kind of preparation methods of aryl aniline compound, include the following steps, S1: organic solvent, water and aniline are added into reaction kettle, bromine, dripping hydrogen peroxide and bromine is added for the first time into reaction kettle, S2: under an inert atmosphere, ether solvent is added into container, is warming up to 40-50 DEG C, then magnesium rod is added into reaction kettle, aryl halide is added dropwise, after being added dropwise to complete;In another container, borate is added into container, is cooled to -5 DEG C -5 DEG C, Grignard Reagent is added dropwise into the container, stands liquid separation, inorganic base is added dropwise in organic phase, extracts liquid separation, then inorganic acid is added dropwise to the water phase after liquid separation, solid is precipitated, obtains aryl boric acid;S3: aryl boric acid and sodium carbonate in step S2 are added in the container of step S1, and catalyst is added, and aryl aniline compound is made in microwave reaction.Under the action of microwave, the rate of coupling reaction is improved, shortens the reaction time, improves the yield of product.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of aryl aniline compound and preparation method thereof.
Background technique
Aromatic amine compounds are a kind of important intermediates, are widely used in the fields such as medicine, dyestuff.Aryl aniline and
The traditional preparation methods of its derivative are that coupling reaction occurs for aryl halides and organic boronic, and aryl aniline compound is made,
This method reaction condition is mild, functional group good compatibility, is widely used in each field, but in traditional synthetic method, virtue
The group steric hindrance of base halides is big, and the reactivity of aryl halides is low, so that the dosage of catalyst is big, coupling reaction
The disadvantages of time is long.
Summary of the invention
It is an object of the invention to: above-mentioned deficiency in the prior art is solved, one kind is provided and efficiently prepares aryl aniline
The method of compound.
To achieve the goals above, the technical solution adopted by the present invention are as follows: a kind of preparation method of aryl aniline compound,
Include the following steps,
S1: organic solvent, water and aniline are added into reaction kettle, magnetic agitation is uniform, is added for the first time into reaction kettle
Bromine after stirring 30-40min, then is added dropwise hydrogen peroxide and bromine, and be sufficiently stirred into reaction kettle simultaneously, stands, obtain bromo
Aniline mixture;
S2: under an inert atmosphere, ether solvent being added into container, is warming up to 40-50 DEG C, then magnesium is added into reaction kettle
Aryl halide is added dropwise into container under stiring for item, and after being added dropwise to complete, Grignard Reagent is made;In another container, Xiang Rong
Borate is added in device, is cooled to -5 DEG C -5 DEG C, the Grignard Reagent is added dropwise into the container, stands liquid separation, is dripped in organic phase
Add inorganic base, extracts liquid separation, then inorganic acid is added dropwise to the water phase after liquid separation, solid is precipitated, obtains aryl boric acid;
S3: aryl boric acid and sodium carbonate in above-mentioned steps S2 are added in the container of the step S1, add water,
It stirs evenly, then loaded catalyst palladium acetate is added into container, container is placed in microwave reactor, in 200-240W
It is reacted under frequency, then extractant is added into reaction kettle, aryl aniline compound is made.
Further, the organic solvent are as follows: one of chlorobenzene, bromobenzene, chloroform, dichlorotoleune, dimethylbenzene.
Further, in the step S1, the molar ratio of the aniline and the bromine is 1:1.5-1:2.
Further, in the step S1, the quality for the bromine being added for the first time is the 60%- of the gross mass of bromine
80%.
Further, in the step S1, the molar ratio of the bromine and the hydrogen peroxide is 1:1-1:1.5.
Further, in the step S2, the ether solvent is ether, tetrahydrofuran, glycol dimethyl ether, fourth
One of ether or a variety of mixing.
Further, in the step S2, the aryl halide is para chlorobromobenzene, in benzotrichloride, parabromotoluene
One kind.
Further, in the step S2, the molar ratio of the Grignard Reagent and the borate is 1:1-3:1.
Further, the borate is one of trimethylborate, triethyl borate, butyl borate.
A kind of aryl aniline compound prepared by the above method.
By adopting the above-described technical solution, the beneficial effects of the present invention are:
In method processed of the invention, in organic solvent, aniline and bromine react and bromoaniline are made, and are preparing bromo
During aniline, hydrogen peroxide joined into container, the hydrogen bromide of generation at bromine simple substance, is improved bromine by hydrogen peroxide
Utilization rate;In the present invention, the aryl boric acid prepared and sodium carbonate, catalyst are added to bromoaniline made from step S1
It in mixture, then is placed in microwave reactor and reacts, contain hydrogen peroxide, hydrogen bromide, bromine simple substance and bromo in bromo mixture
Aniline, under the effect of the catalyst, bromoaniline and aryl boric acid occur coupling reaction and improve coupling under the action of microwave
The rate of reaction is closed, and due to existing simultaneously hydrogen peroxide and bromine in coupling reaction system, is made jointly with palladium acetate catalyst
With raising reaction rate shortens the reaction time, improves the yield of product.
Specific embodiment
Embodiment 1:
50 parts of chlorobenzenes, 50 parts of water and 10 parts of aniline are added into three neck round bottom flask, magnetic agitation is uniform, then to reaction
It is added at one time 9 parts of bromines in kettle, after stirring 40min, then 6 parts of bromines is taken to be placed in buret, 15 parts of hydrogen peroxide is taken to be placed in
In another buret, two burets are mounted on round-bottomed flask, while into round-bottomed flask, being added dropwise with same speed
Hydrogen peroxide and bromine are sufficiently stirred during dropwise addition, after being added dropwise to complete, stand, obtain bromoaniline mixture;
Another container is taken, under an inert atmosphere, 50 parts of tetrahydrofurans are added into container, by the tetrahydrofuran water-bath of container
50 DEG C are warming up to, then magnesium rod is added into reaction kettle, under stiring, para chlorobromobenzene is added dropwise into container, after being added dropwise to complete, cooling
To room temperature, stand for standby use is made Grignard Reagent, takes in another container, and 10 parts of trimethylborates are added into container, container is existed
It is cooled to -5 DEG C in ice bath, 10 parts of Grignard Reagent obtained are being added dropwise into the container, after being added dropwise to complete, are standing liquid separation, Xiang You
Sodium carbonate is added dropwise in machine phase, extracts liquid separation, then dilute hydrochloric acid is added dropwise in the water phase having to liquid separation, solid is precipitated to get phenyl boric acid is arrived;
20 parts of phenyl boric acids obtained and 10 parts of sodium carbonate are added in the container equipped with 10 parts of bromoaniline mixtures, then
Water is added, stirs evenly, then 1 part of loaded catalyst palladium acetate is added into container, container is placed in microwave reactor,
20min is reacted under 200W frequency, then extractant is added into reaction kettle, aryl aniline compound is made, and product yield is
91%.
Embodiment 2:
50 parts of bromobenzenes, 50 parts of water and 10 parts of aniline are added into three neck round bottom flask, magnetic agitation is uniform, then to reaction
It is added at one time 12 parts of bromines in kettle, after stirring 40min, then 8 parts of bromines is taken to be placed in buret, 20 parts of hydrogen peroxide is taken to be placed in
In another buret, two burets are mounted on round-bottomed flask, while into round-bottomed flask, being added dropwise with same speed
Hydrogen peroxide and bromine are sufficiently stirred during dropwise addition, after being added dropwise to complete, stand, obtain bromoaniline mixture;
Another container is taken, under an inert atmosphere, 50 parts of ether are added into container, by the ether warming-in-water of container to 40
DEG C, then magnesium rod is added into reaction kettle, under stiring, benzotrichloride is added dropwise into container, after being added dropwise to complete, is cooled to room temperature,
Stand for standby use is made Grignard Reagent, takes in another container, 10 parts of triethyl borates is added into container, by container in ice bath
- 5 DEG C are cooled to, 20 parts of Grignard Reagent obtained are being added dropwise into the container, after being added dropwise to complete, liquid separation are being stood, into organic phase
Sodium carbonate is added dropwise, extracts liquid separation, then dilute hydrochloric acid is added dropwise in the water phase having to liquid separation, solid is precipitated to get toluene boric acid is arrived;
20 parts of toluene boric acid obtained and 8 parts of sodium carbonate are added in the container equipped with 10 parts of bromoaniline mixtures,
Water is added, is stirred evenly, then 1 part of loaded catalyst palladium acetate is added into container, container is placed on microwave reactor
In, 30min being reacted under 241W frequency, then extractant is added into reaction kettle, aryl aniline compound being made, product yield is
93.2%.
Embodiment 3:
It is equal that 25 parts of chloroforms, 25 parts of dichlorotoleune, 50 parts of water and 10 parts of aniline, magnetic agitation are added into three neck round bottom flask
It is even, then to 16 parts of bromines are added at one time in reaction kettle, after stirring 30min, then 4 parts of bromines are taken to be placed in buret, taken
20 parts of hydrogen peroxide are placed in another buret, two burets are mounted on round-bottomed flask, while into round-bottomed flask, with substantially
Hydrogen peroxide is added dropwise in identical speed and bromine is sufficiently stirred during dropwise addition, after being added dropwise to complete, stands, obtains bromobenzene
Amine blends;
Another container is taken, under an inert atmosphere, 50 parts of glycol dimethyl ethers are added into container, by the ethylene glycol two of container
Methyl ether warming-in-water is to 45 DEG C, then magnesium rod is added into reaction kettle, under stiring, parabromotoluene is added dropwise into container, drips
Cheng Hou is cooled to room temperature, and stand for standby use is made Grignard Reagent, takes in another container, and 10 parts of three fourths of boric acid are added into container
Container is cooled to 0 DEG C by ester in ice bath, and 30 parts of Grignard Reagent obtained are being added dropwise into the container, after being added dropwise to complete, are standing
Sodium carbonate is added dropwise into organic phase for liquid separation, extracts liquid separation, then dilute hydrochloric acid is added dropwise in the water phase having to liquid separation, and solid is precipitated to get arriving
Toluene boric acid;
15 parts of toluene boric acid obtained and 10 parts of sodium carbonate are added in the container equipped with 15 parts of bromoaniline mixtures,
Water is added, is stirred evenly, then 1 part of loaded catalyst palladium acetate is added into container, container is placed on microwave reactor
In, 20min being reacted under 240W frequency, then extractant is added into reaction kettle, aryl aniline compound being made, product yield is
89.5%.
Embodiment 4:
50 parts of dimethylbenzene, 50 parts of water and 20 parts of aniline are added into three neck round bottom flask, magnetic agitation is uniform, then to anti-
It answers and is added at one time 18 parts of bromines in kettle, after stirring 40min, then 12 parts of bromines is taken to be placed in buret, take 45 parts of hydrogen peroxide
It is placed in another buret, two burets is mounted on round-bottomed flask, while into round-bottomed flask, with same speed
Hydrogen peroxide is added dropwise and bromine is sufficiently stirred during dropwise addition, after being added dropwise to complete, stands, obtains bromoaniline mixture;
Another container is taken, under an inert atmosphere, 50 parts of glycol dimethyl ethers are added into container, by the ethylene glycol two of container
Methyl ether warming-in-water is to 40 DEG C, then magnesium rod is added into reaction kettle, under stiring, parabromotoluene is added dropwise into container, drips
Cheng Hou is cooled to room temperature, and stand for standby use is made Grignard Reagent, takes in another container, and 10 parts of three fourths of boric acid are added into container
Container is cooled to 5 DEG C by ester in ice bath, and 10 parts of Grignard Reagent obtained are being added dropwise into the container, after being added dropwise to complete, are standing
Sodium carbonate is added dropwise into organic phase for liquid separation, extracts liquid separation, then dilute hydrochloric acid is added dropwise in the water phase having to liquid separation, and solid is precipitated to get arriving
Phenyl boric acid;
20 parts of phenyl boric acids obtained and 10 parts of sodium carbonate are added in the container equipped with 10 parts of bromoaniline mixtures, then
Water is added, stirs evenly, then 1 part of palladium acetate of loaded catalyst is added into container, container is placed in microwave reactor,
20min is reacted under 230W frequency, then extractant is added into reaction kettle, aryl aniline compound is made, and product yield is
94.6%.
Embodiment 5:
50 parts of dichlorotoleune, 50 parts of water and 10 parts of aniline are added into three neck round bottom flask, magnetic agitation is uniform, then to
It is added at one time 14 parts of bromines in reaction kettle, after stirring 40min, then 6 parts of bromines is taken to be placed in buret, takes 20 parts of hydrogen peroxide
It is placed in another buret, two burets is mounted on round-bottomed flask, while into round-bottomed flask, with same speed
Hydrogen peroxide is added dropwise and bromine is sufficiently stirred during dropwise addition, after being added dropwise to complete, stands, obtains bromoaniline mixture;
Another container is taken, under an inert atmosphere, 50 parts of butyl ether are added into container, by the butyl ether warming-in-water of container to 40
DEG C, then magnesium rod is added into reaction kettle, under stiring, benzotrichloride is added dropwise into container, after being added dropwise to complete, is cooled to room temperature,
Stand for standby use is made Grignard Reagent, takes in another container, 10 parts of trimethylborates is added into container, by container in ice bath
2 DEG C are cooled to, 10 parts of Grignard Reagent obtained are being added dropwise into the container, after being added dropwise to complete, is standing liquid separation, is dripped into organic phase
Add sodium carbonate, extract liquid separation, then dilute hydrochloric acid is added dropwise in the water phase having to liquid separation, solid is precipitated to get phenyl boric acid is arrived;
20 parts of phenyl boric acids obtained and 8 parts of sodium carbonate are added in the container equipped with 8 parts of bromoaniline mixtures, then plus
Enter water, stir evenly, then 1 part of palladium acetate of loaded catalyst is added into container, container is placed in microwave reactor,
20min is reacted under 230W frequency, then extractant is added into reaction kettle, aryl aniline compound is made, and product yield is
83.2%.
In the embodiment of the present invention 1-5, the yield of product is 80% or more, and reaction efficiency is high, and the reaction time is short.
Claims (10)
1. a kind of preparation method of aryl aniline compound, it is characterised in that: include the following steps,
S1: organic solvent, water and aniline being added into container, and magnetic agitation is uniform, and bromine is added for the first time into container, stir
After 30-40min, then hydrogen peroxide and bromine is added dropwise into reaction kettle simultaneously, and be sufficiently stirred, obtains bromoaniline mixture;
S2: under an inert atmosphere, ether solvent is added into another container, is warming up to 40-50 DEG C, then magnesium is added into reaction kettle
Aryl halide is added dropwise into container under stiring for item, and after being added dropwise to complete, Grignard Reagent is made;In another container, Xiang Rong
Borate is added in device, is cooled to -5 DEG C -5 DEG C, the Grignard Reagent is added dropwise into the container, stands liquid separation, is dripped in organic phase
Add inorganic base, extracts liquid separation, then inorganic acid is added dropwise to the water phase after liquid separation, solid is precipitated, obtains aryl boric acid;
S3: aryl boric acid and sodium carbonate in above-mentioned steps S2 are added in the container of the step S1, add water, stirring
Uniformly, then into container loaded catalyst palladium acetate is added, container is placed in microwave reactor, in 200-240W frequency
Lower reaction, then extractant is added into reaction kettle, aryl aniline compound is made.
2. the preparation method of aryl aniline compound according to claim 1, it is characterised in that: the organic solvent are as follows:
One of chlorobenzene, bromobenzene, chloroform, dichlorotoleune, dimethylbenzene.
3. the preparation method of aryl aniline compound according to claim 1, it is characterised in that: in the step S1,
The molar ratio of the aniline and the bromine is 1:1.5-1:2.
4. the preparation method of aryl aniline compound according to claim 1, it is characterised in that: in the step S1,
The quality for the bromine being added for the first time is the 60%-80% of the gross mass of bromine.
5. the preparation method of aryl aniline compound according to claim 1, it is characterised in that: in the step S1,
The molar ratio of the bromine and the hydrogen peroxide is 1:1-1:1.5.
6. the preparation method of aryl aniline compound according to claim 1, it is characterised in that: in the step S2
In, the ether solvent is one of ether, tetrahydrofuran, glycol dimethyl ether, butyl ether or a variety of mixing.
7. the preparation method of aryl aniline compound according to claim 1, it is characterised in that: in the step S2,
The aryl halide is para chlorobromobenzene, benzotrichloride, a kind of in parabromotoluene.
8. the preparation method of aryl aniline compound according to claim 1, it is characterised in that: in the step S2,
The Grignard Reagent and the molar ratio of the borate are 1:1-3:1.
9. the preparation method of aryl aniline compound according to claim 1, it is characterised in that: the borate is boron
One of sour trimethyl, triethyl borate, butyl borate.
10. a kind of aryl aniline compound prepared by the preparation method by any aryl aniline compound of claim 1-9.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811624099.7A CN109608341A (en) | 2018-12-28 | 2018-12-28 | A kind of aryl aniline compound and preparation method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811624099.7A CN109608341A (en) | 2018-12-28 | 2018-12-28 | A kind of aryl aniline compound and preparation method thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
CN109608341A true CN109608341A (en) | 2019-04-12 |
Family
ID=66013061
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811624099.7A Pending CN109608341A (en) | 2018-12-28 | 2018-12-28 | A kind of aryl aniline compound and preparation method thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109608341A (en) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006118155A1 (en) * | 2005-04-27 | 2006-11-09 | Ishihara Sangyo Kaisha, Ltd. | Biphenyl derivative or salt thereof, and bactericide for agricultural and horticultural use containing same as active ingredient |
CN101928224A (en) * | 2009-06-18 | 2010-12-29 | 巨野金岭生物科技发展有限公司 | Method for preparing tribromoaniline by peroxide bromination method |
CN103570753A (en) * | 2013-11-13 | 2014-02-12 | 大连九信生物化工科技有限公司 | Preparation method of arylboronic acid compound |
CN104119367A (en) * | 2014-07-09 | 2014-10-29 | 中国科学技术大学苏州研究院 | Preparation method of aryl boric acid |
CN104530106A (en) * | 2014-12-30 | 2015-04-22 | 京博农化科技股份有限公司 | Method for preparing arylboronic acid compound |
CN106892865A (en) * | 2015-12-19 | 2017-06-27 | 西安瑞联新材料股份有限公司 | A kind of synthetic method of the chloro- 6- p-methylphenyls quinoline of 2,4- bis- |
-
2018
- 2018-12-28 CN CN201811624099.7A patent/CN109608341A/en active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006118155A1 (en) * | 2005-04-27 | 2006-11-09 | Ishihara Sangyo Kaisha, Ltd. | Biphenyl derivative or salt thereof, and bactericide for agricultural and horticultural use containing same as active ingredient |
CN101928224A (en) * | 2009-06-18 | 2010-12-29 | 巨野金岭生物科技发展有限公司 | Method for preparing tribromoaniline by peroxide bromination method |
CN103570753A (en) * | 2013-11-13 | 2014-02-12 | 大连九信生物化工科技有限公司 | Preparation method of arylboronic acid compound |
CN104119367A (en) * | 2014-07-09 | 2014-10-29 | 中国科学技术大学苏州研究院 | Preparation method of aryl boric acid |
CN104530106A (en) * | 2014-12-30 | 2015-04-22 | 京博农化科技股份有限公司 | Method for preparing arylboronic acid compound |
CN106892865A (en) * | 2015-12-19 | 2017-06-27 | 西安瑞联新材料股份有限公司 | A kind of synthetic method of the chloro- 6- p-methylphenyls quinoline of 2,4- bis- |
Non-Patent Citations (6)
Title |
---|
NICHOLAS E. LEADBEATER 等: "Use of a scientific microwave apparatus for rapid optimization of reaction conditions in a monomode function and then substrate screening in a multimode function", 《TETRAHEDRON》 * |
刘宁 等: "水相钯催化SUZUKI反应", 《有机化学》 * |
孙斌 等: "水-有机两相体系中Pd(OAc)2催化的SUZUKI反应与2-(4-氯苯基)苯胺的合成", 《化学研究与应用》 * |
白林: "微波促进环境友好的SUZUKI芳基偶联反应研究", 《中国优秀博硕士学位论文全文数据库(博士)工程科技I辑》 * |
薛亮 等: "2-(3,4-二氯苯基)-4-氟苯胺的合成工艺研究", 《精细化工中间体》 * |
赵晓伟 等: "微波技术在SUZUKI反应中的应用", 《化学进展》 * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102924301B (en) | Preparation method of N,N-bis(2-hydroxyethyl)isopropanolamine | |
CN110776649B (en) | Cadmium-organic supramolecular polymer containing anthracene group and preparation method and application thereof | |
CN104530106A (en) | Method for preparing arylboronic acid compound | |
CN109608341A (en) | A kind of aryl aniline compound and preparation method thereof | |
CN104926668B (en) | A kind of preparation method of tri-long-chain alkyl ammonium bicarbonate and carbonate | |
CN101890366A (en) | Cupric salt-containing catalyst system and application thereof | |
CN109575063B (en) | Boron esterification reaction method of alkyl halide without transition metal catalysis | |
CN108440251A (en) | A kind of method of light/nickel concerted catalysis list arylation glycol | |
CN105153059B (en) | The preparation method of Yi Zhong oxazolidinone compounds | |
CN104447506B (en) | The preparation method of the alkyl carbazole of 2 acetyl group 9 | |
CN104926633A (en) | Preparation method for 3-alkoxybenzaldehyde | |
CN103381359A (en) | Preparation method for catalyst for N,N-dimethyl-caprylamide/decanamide | |
CN208671722U (en) | A kind of phenylene dimethyl ether high-effect cooling device | |
CN106631968A (en) | Method for preparing indole and derivatives thereof | |
CN101830763B (en) | Application of nickel catalyst in suzuki-miyaura coupling reaction | |
CN105462285A (en) | Synthesis method of disperse red F3BS | |
CN110105382A (en) | 1,1,2,2- tetraboric acid ester ethylene and its preparation method and application | |
CN109503338A (en) | A method of preparing cis- trifluoromethyl styrene compound | |
CN108191601A (en) | A kind of synthetic method of 4- cyclopenta biphenyl fluorochemical | |
CN109021002B (en) | Preparation method of naphthalene-1, 8-diamino aryl boron amide | |
CN104447293B (en) | A kind of method preparing 1-methylcyclopropyl groups formic acid | |
CN113880698B (en) | Preparation method of 9, 10-dibutoxyanthracene | |
WO2022214045A1 (en) | Method for preparing deuterated chemical by means of deuteration reaction of carbon-hydrogen bond with deuterium gas under catalysis of alkali | |
CN108586262A (en) | A kind of synthetic method of the asymmetric Terphenyls compound based on one kettle way | |
CN102863344B (en) | Preparation method of tomoxetine medicine |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190412 |
|
RJ01 | Rejection of invention patent application after publication |