CN102126962A - Method for preparing 2,4,6-triaryl phenylamine compound in aqueous phase - Google Patents
Method for preparing 2,4,6-triaryl phenylamine compound in aqueous phase Download PDFInfo
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- CN102126962A CN102126962A CN2011100277294A CN201110027729A CN102126962A CN 102126962 A CN102126962 A CN 102126962A CN 2011100277294 A CN2011100277294 A CN 2011100277294A CN 201110027729 A CN201110027729 A CN 201110027729A CN 102126962 A CN102126962 A CN 102126962A
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- triaryl
- aqueous phase
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- aniline compound
- boric acid
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- -1 phenylamine compound Chemical class 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000008346 aqueous phase Substances 0.000 title claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 20
- 239000004327 boric acid Substances 0.000 claims abstract description 18
- 238000004440 column chromatography Methods 0.000 claims abstract description 15
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 14
- 239000012074 organic phase Substances 0.000 claims abstract description 12
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 238000006069 Suzuki reaction reaction Methods 0.000 claims abstract description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 24
- 235000010338 boric acid Nutrition 0.000 claims description 19
- 229950001336 bromamide Drugs 0.000 claims description 15
- 239000012141 concentrate Substances 0.000 claims description 11
- 235000002639 sodium chloride Nutrition 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- QFNFDUFAPXVTAW-UHFFFAOYSA-M [OH-].[K+].[PH2](=O)O Chemical compound [OH-].[K+].[PH2](=O)O QFNFDUFAPXVTAW-UHFFFAOYSA-M 0.000 claims description 9
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 4
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 claims description 3
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 claims description 3
- 125000005619 boric acid group Chemical class 0.000 claims description 3
- XLGLMVCAOMQNJT-UHFFFAOYSA-N boric acid;chlorobenzene Chemical compound OB(O)O.ClC1=CC=CC=C1 XLGLMVCAOMQNJT-UHFFFAOYSA-N 0.000 claims description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- 235000017550 sodium carbonate Nutrition 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 45
- 239000000047 product Substances 0.000 abstract description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 16
- 238000000926 separation method Methods 0.000 abstract description 11
- 239000011261 inert gas Substances 0.000 abstract description 2
- GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- 230000036632 reaction speed Effects 0.000 abstract 1
- 239000012266 salt solution Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 9
- 238000005303 weighing Methods 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 5
- AGWKGKUGJDMKMT-UHFFFAOYSA-N 2,4,6-triphenylaniline Chemical compound NC1=C(C=2C=CC=CC=2)C=C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 AGWKGKUGJDMKMT-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- WGURSKWDHNBQAD-UHFFFAOYSA-N 4-(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N)C=C1 WGURSKWDHNBQAD-UHFFFAOYSA-N 0.000 description 1
- XQXQEZXUJOCXCN-UHFFFAOYSA-N 4-(aminomethyl)-n-phenylaniline Chemical compound C1=CC(CN)=CC=C1NC1=CC=CC=C1 XQXQEZXUJOCXCN-UHFFFAOYSA-N 0.000 description 1
- HTPGFCKKCPBMTH-UHFFFAOYSA-N 4-chloro-2-phenylaniline Chemical compound NC1=CC=C(Cl)C=C1C1=CC=CC=C1 HTPGFCKKCPBMTH-UHFFFAOYSA-N 0.000 description 1
- RBWCFTJQRDTIBX-UHFFFAOYSA-N 4-fluoro-n-phenylaniline Chemical compound C1=CC(F)=CC=C1NC1=CC=CC=C1 RBWCFTJQRDTIBX-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing a 2,4,6-triaryl phenylamine compound in an aqueous phase. In the method, the 2,4,6-triaryl phenylamine compound is prepared by performing a Suzuki cross coupling reaction on 2,4,6-tribromophenylamine and aryl boric acid. The method comprises the following steps of: adding the 2,4,6-tribromophenylamine, the aryl boric acid, alkali and a catalyst according to a molar ratio of 0.25:1.125:1.25:0.0025 into N,N-dimethylformamide (DMF)/H2O (2.7 mL/1.3 mL); reacting in the air at the temperature of 80 DEG C for 15 to 80 minutes; after the reaction is finished, adding saturated salt solution; extracting a reaction product by using ethyl acetate; mixing organic phases; concentrating; and separating by a column chromatography to obtain the analytically pure 2,4,6-triaryl phenylamine compound. The method has the characteristics of no ligand, phase transfer agent or accelerator, no protection of inert gas, environmental friendliness, low using amount of a palladium catalyst, high reaction speed, high yield and simpleness in product separation.
Description
Technical field
The present invention relates to a kind of in aqueous phase preparation 2,4, the method for 6-triaryl aniline compound, it belongs to the organic compound technical field of catalytic chemistry.
Background technology
2,4,6-triaryl aniline compound is widely used in preparation (the Bioorg. Med. Chem. Lett. 2007,3208 of medicine, dyestuff, high-spin or magneticsubstance etc.; Tetrahedron 2000,5435; Macromol. Rapid Commun. 2003,768; Polyhedron 2002,1305; J. Org. Chem. 2001,7456; J. Org. Chem. 2003,1225; J. Org. Chem. 1991,6638).2,4,6-triaryl aniline compound can be obtained by the nitro-compound reduction, but its reaction conditions very harsh (J. Chem. Soc., Dalton Trans. 1996,4265).The catalytic Suzuki linked reaction of palladium is preparation 2,4, one of effective means of 6-triaryl aniline structure.So far, the preparation 2,4 of bibliographical information, the method for 6-triaryl aniline compound need be used air and water sensitive, synthetic difficulty, expensive phosphine part are promoted, and the reaction times is grown (Synthesis 1995,1419).Thereby development is simple, cheap, it is general 2,4 efficiently to reach, and the preparation method of 6-triaryl aniline compound has the important application prospect.
In recent years, bibliographical information do not need the promoted Suzuki reaction system of part to prepare 2,4,6-triaryl aniline compound (Green Chem. 2003,635; Tetrahedron Lett. 2003,3817).Yet deficiency such as these methods exist still that catalyst levels is big, reactive behavior is low, long reaction time or productive rate are lower.Do not appear in the newspapers so far and need not part and promote and efficiently to activate 2,4 that the 6-bromamide is used for Suzuki prepared in reaction 2,4, the method for 6-triaryl substituted aniline derivative.
Summary of the invention
The purpose of this invention is to provide a kind of simple to operate, cheap, high reactivity, in the palladium catalysis 2,4 that aqueous phase carries out, the Suzuki cross-coupling reaction of 6-bromamide and aryl boric acid preparation 2,4, the catalysis novel process of 6-triaryl aniline compound.
The technical scheme that adopts is: provide a kind of in aqueous phase preparation 2,4, the method for 6-triaryl aniline compound, in air atmosphere, with 2,4,6-bromamide, aryl boric acid, alkali and palladium catalyst are added to DMF/H for 1:4.5-6.5:4.5-5.5:0.005-0.02 in molar ratio
2O is the N of 1 mL/3 mL-3 mL/1 mL, in the dinethylformamide solution, stir at 50-100 ° of C and to carry out the Suzuki(Suzuki) cross-coupling reaction 15～80 minutes, reaction is used the ethyl acetate extraction reaction product after finishing, merge organic phase, concentrate, use column chromatography, make analytically pure 2,4,6-triaryl aniline compound.
According to provided by the invention a kind of in aqueous phase preparation 2,4, method one optimal technical scheme of 6-triaryl aniline compound is: before with the ethyl acetate extraction reaction product, add saturated aqueous common salt.
According to provided by the invention a kind of in aqueous phase preparation 2,4, method one optimal technical scheme of 6-triaryl aniline compound is: described 2,4,6-bromamide, aryl boric acid, alkali and palladium catalyst are 0.25: 1.125: 1.25 in molar ratio: 0.0025.
According to provided by the invention a kind of in aqueous phase preparation 2,4, method one optimal technical scheme of 6-triaryl aniline compound is: described N, the DMF/H of dinethylformamide solution
2O is 2.7 mL/1.3 mL.
According to provided by the invention a kind of in aqueous phase preparation 2,4, method one optimal technical scheme of 6-triaryl aniline compound is: the temperature of reaction of described Suzuki cross-coupling reaction is 80 ° of C.
According to provided by the invention a kind of in aqueous phase preparation 2,4, method one optimal technical scheme of 6-triaryl aniline compound is: described palladium catalyst is selected from palladium or Palladous chloride.
According to provided by the invention a kind of in aqueous phase preparation 2,4, method one optimal technical scheme of 6-triaryl aniline compound is: described alkali is selected from seven hypophosphite monohydrate potassium, salt of wormwood or yellow soda ash.
According to provided by the invention a kind of in aqueous phase preparation 2,4, method one optimal technical scheme of 6-triaryl aniline compound is: described aryl boric acid is selected from phenylo boric acid, 4-methylphenylboronic acid, 4-methoxyphenylboronic acid, 4-fluorobenzoic boric acid, 3,4-two fluorobenzoic boric acids or 4-chlorobenzene boric acid.
The invention has the beneficial effects as follows: this 2; 4; the preparation method of 6-triaryl aniline compound does not use part or promotor, does not need protection of inert gas, reaction under mild conditions, palladium catalyst consumption are few; reaction fast, yield is high, product separation is simple, has a wide range of applications at aspects such as medicine, dyestuff, part, high-spin or magneticsubstance synthesize.
Embodiment
The present invention is described in detail below in conjunction with specific embodiment.
Embodiment 12,4,6-triphenyl aniline
In air, take by weighing 2,4 successively, 6-bromamide (0.25 mmol), phenylo boric acid (1.125 mmol), seven hypophosphite monohydrate potassium (1.25 mmol), palladium (0.0025 mmol) also is transferred in two mouthfuls of bottles of 25 mL, adds DMF/H subsequently in two mouthfuls of bottles of 25 mL
2O(2.7 mL/1.3 mL).At 80 ° of C lower magnetic force stirring reaction 30 min, thin-layer chromatography is followed the tracks of reaction.Reaction finishes the back and adds 15 mL saturated aqueous common salts also with ethyl acetate (15 mL 3) extractive reaction product, merge organic phase, use Rotary Evaporators concentrate thick product, column chromatography obtains target product, the elutriant that column chromatography is used is ethyl acetate/petroleum ether (V/V=1/200), and product structure passes through
1H NMR and mass spectrum are identified.Separation yield reaches 99%.
Embodiment 22,4,6-triphenyl aniline
In air, take by weighing 2,4 successively, 6-bromamide (0.25 mmol), phenylo boric acid (1.125 mmol), seven hypophosphite monohydrate potassium (1.25 mmol), Palladous chloride (0.0025 mmol) also is transferred in two mouthfuls of bottles of 25 mL, adds DMF/H subsequently in two mouthfuls of bottles of 25 mL
2O(2.7 mL/1.3 mL).At 80 ° of C lower magnetic force stirring reaction 60 min, thin-layer chromatography is followed the tracks of reaction.Reaction finishes the back and adds 15 mL saturated aqueous common salts and with ethyl acetate (15 mL 3) extractive reaction product, merge organic phase, use Rotary Evaporators concentrate thick product, separation yield reaches 91%.
Embodiment 32,4,6-triphenyl aniline
In air, take by weighing 2,4 successively, 6-bromamide (0.25 mmol), phenylo boric acid (1.125 mmol), salt of wormwood (1.25 mmol), palladium (0.0025 mmol) also is transferred in two mouthfuls of bottles of 25 mL, adds DMF/H subsequently in two mouthfuls of bottles of 25 mL
2O(2.7 mL/1.3 mL).At 80 ° of C lower magnetic force stirring reaction 60 min, thin-layer chromatography is followed the tracks of reaction.Reaction finishes the back and adds 15 mL saturated aqueous common salts and with ethyl acetate (15 mL 3) extractive reaction product, merge organic phase, use Rotary Evaporators concentrate thick product, separation yield reaches 99%.
Embodiment 42,4,6-triphenyl aniline
In air, take by weighing 2,4 successively, 6-bromamide (0.25 mmol), phenylo boric acid (1.125 mmol), yellow soda ash (1.25 mmol), palladium (0.0025 mmol) also is transferred in two mouthfuls of bottles of 25 mL, adds DMF/H subsequently in two mouthfuls of bottles of 25 mL
2O(2.7 mL/1.3 mL).At 80 ° of C lower magnetic force stirring reaction 60 min, thin-layer chromatography is followed the tracks of reaction.Reaction finishes the back and adds 15 mL saturated aqueous common salts and with ethyl acetate (15 mL 3) extractive reaction product, merge organic phase, use Rotary Evaporators concentrate thick product, separation yield reaches 99%.
Embodiment 52,4,6-three (4-aminomethyl phenyl) aniline
In air, take by weighing 2,4 successively, 6-bromamide (0.25 mmol), 4-methylphenylboronic acid (1.125 mmol), seven hypophosphite monohydrate potassium (1.25 mmol), palladium (0.0025 mmol) also is transferred in two mouthfuls of bottles of 25 mL, adds DMF/H subsequently in two mouthfuls of bottles of 25 mL
2O(2.7 mL/1.3 mL).At 80 ° of C lower magnetic force stirring reaction 55 min, thin-layer chromatography is followed the tracks of reaction.Reaction finishes the back and adds 15 mL saturated aqueous common salts also with ethyl acetate (15 mL 3) extractive reaction product, merge organic phase, use Rotary Evaporators concentrate thick product, column chromatography obtains target product, the elutriant that column chromatography is used is ethyl acetate/petroleum ether (V/V=1/300), and product structure passes through
1H NMR and mass spectrum are identified.Separation yield reaches 86%.
Embodiment 62,4,6-three (4-p-methoxy-phenyl) aniline
In air, take by weighing 2,4 successively, 6-bromamide (0.25 mmol), 4-methoxyphenylboronic acid (1.125 mmol), seven hypophosphite monohydrate potassium (1.25 mmol), palladium (0.0025 mmol) also is transferred in two mouthfuls of bottles of 25 mL, adds DMF/H subsequently in two mouthfuls of bottles of 25 mL
2O(2.7 mL/1.3 mL).At 80 ° of C lower magnetic force stirring reaction 80 min, thin-layer chromatography is followed the tracks of reaction.Reaction finishes the back and adds 15 mL saturated aqueous common salts also with ethyl acetate (15 mL 3) extractive reaction product, merge organic phase, use Rotary Evaporators concentrate thick product, column chromatography obtains target product, the elutriant that column chromatography is used is ethyl acetate/petroleum ether (V/V=1/10), and product structure passes through
1H NMR and mass spectrum are identified.Separation yield reaches 82%.
Embodiment 72,4,6-three (4-fluorophenyl) aniline
In air, take by weighing 2,4 successively, 6-bromamide (0.25 mmol), 4-fluorobenzoic boric acid (1.125 mmol), seven hypophosphite monohydrate potassium (1.25 mmol), palladium (0.0025 mmol) also is transferred in two mouthfuls of bottles of 25 mL, adds DMF/H subsequently in two mouthfuls of bottles of 25 mL
2O(2.7 mL/1.3 mL).At 80 ° of C lower magnetic force stirring reaction 40 min, thin-layer chromatography is followed the tracks of reaction.Reaction finishes the back and adds 15 mL saturated aqueous common salts also with ethyl acetate (15 mL 3) extractive reaction product, merge organic phase, use Rotary Evaporators concentrate thick product, column chromatography obtains target product, the elutriant that column chromatography is used is ethyl acetate/petroleum ether (V/V=1/300), and product structure passes through
1H NMR and mass spectrum are identified.Separation yield reaches 93%.
Embodiment 82,4,6-three (3, the 4-difluorophenyl) aniline
In air, take by weighing 2,4 successively, 6-bromamide (0.25 mmol), 3,4-two fluorobenzoic boric acids (1.125 mmol), palladium (0.0025 mmol), seven hypophosphite monohydrate potassium (1.25 mmol) also are transferred in two mouthfuls of bottles of 25 mL, add DMF/H subsequently in two mouthfuls of bottles of 25 mL
2O(2.7 mL/1.3 mL).At 80 ° of C lower magnetic force stirring reaction 15 min, thin-layer chromatography is followed the tracks of reaction.Reaction finishes the back and adds 15 mL saturated aqueous common salts also with ethyl acetate (15 mL 3) extractive reaction product, merge organic phase, use Rotary Evaporators concentrate thick product, column chromatography obtains target product, the elutriant that column chromatography is used is ethyl acetate/petroleum ether (V/V=1/200), and product structure passes through
1H NMR and mass spectrum are identified.Separation yield reaches 87%.
Embodiment 92,4,6-three (4-chloro-phenyl-) aniline
In air, take by weighing 2,4 successively, 6-bromamide (0.25 mmol), 4-chlorobenzene boric acid (1.125 mmol), palladium (0.0025 mmol), seven hypophosphite monohydrate potassium (1.25 mmol) also are transferred in two mouthfuls of bottles of 25 mL, add DMF/H subsequently in two mouthfuls of bottles of 25 mL
2O(2.7 mL/1.3 mL).At 80 ° of C lower magnetic force stirring reaction 35 min, thin-layer chromatography is followed the tracks of reaction.Reaction finishes the back and adds 15 mL saturated aqueous common salts also with ethyl acetate (15 mL 3) extractive reaction product, merge organic phase, use Rotary Evaporators concentrate thick product, column chromatography obtains target product, the elutriant that column chromatography is used is pure sherwood oil, and product structure passes through
1H NMR and mass spectrum are identified.Separation yield reaches 96%.
Above content be in conjunction with optimal technical scheme to further describing that the present invention did, can not assert that the concrete enforcement of invention only limits to these explanations.Concerning the general technical staff of the technical field of the invention, under the prerequisite that does not break away from design of the present invention, can also make simple deduction and replacement, all should be considered as protection scope of the present invention.
Claims (8)
1. one kind in aqueous phase preparation 2,4, the method for 6-triaryl aniline compound, it is characterized in that: in air atmosphere, with 2,4,6-bromamide, aryl boric acid, alkali and palladium catalyst are added to DMF/H for 1:4.5-6.5:4.5-5.5:0.005-0.02 in molar ratio
2O is the N of 1 mL/3 mL-3 mL/1 mL, in the dinethylformamide solution, carried out Suzuki Suzuki cross-coupling reaction 15～80 minutes 50-100 ° of C stirring, reaction is used the ethyl acetate extraction reaction product after finishing, merge organic phase, concentrate, use column chromatography, make analytically pure 2,4,6-triaryl aniline compound.
2. according to claim 1 a kind of in aqueous phase preparation 2,4, the method for 6-triaryl aniline compound is characterized in that: before with the ethyl acetate extraction reaction product, add saturated aqueous common salt.
3. according to claim 1 a kind of in aqueous phase preparation 2,4, the method for 6-triaryl aniline compound is characterized in that: described 2,4,6-bromamide, aryl boric acid, alkali and palladium catalyst are 0.25: 1.125: 1.25 in molar ratio: 0.0025.
4. according to claim 1 a kind of in aqueous phase preparation 2,4, the method for 6-triaryl aniline compound is characterized in that: described N, the DMF/H of dinethylformamide solution
2O is 2.7 mL/1.3 mL.
5. according to claim 1 a kind of in aqueous phase preparation 2,4, the method for 6-triaryl aniline compound is characterized in that: the temperature of reaction of described Suzuki cross-coupling reaction is 80 ° of C.
6. according to claim 1 a kind of in aqueous phase preparation 2,4, the method for 6-triaryl aniline compound is characterized in that: described palladium catalyst is selected from palladium or Palladous chloride.
7. according to claim 1 a kind of in aqueous phase preparation 2,4, the method for 6-triaryl aniline compound is characterized in that: described alkali is selected from seven hypophosphite monohydrate potassium, salt of wormwood or yellow soda ash.
8. according to claim 1 a kind of in aqueous phase preparation 2,4, the method of 6-triaryl aniline compound is characterized in that: described aryl boric acid is selected from phenylo boric acid, 4-methylphenylboronic acid, 4-methoxyphenylboronic acid, 4-fluorobenzoic boric acid, 3,4-two fluorobenzoic boric acids or 4-chlorobenzene boric acid.
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Cited By (1)
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| CN105439871A (en) * | 2015-12-02 | 2016-03-30 | 北京格林凯默科技有限公司 | Preparation method of aminobiphenyl compounds |
| CN105439871B (en) * | 2015-12-02 | 2017-10-31 | 北京格林凯默科技有限公司 | A kind of preparation method of aminobiphenyl compounds |
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Application publication date: 20110720 |