CN104529786A - Method for synthesizing 3,4,5-trifluoro-2'-nitrobiphenyl - Google Patents
Method for synthesizing 3,4,5-trifluoro-2'-nitrobiphenyl Download PDFInfo
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- CN104529786A CN104529786A CN201410785170.5A CN201410785170A CN104529786A CN 104529786 A CN104529786 A CN 104529786A CN 201410785170 A CN201410785170 A CN 201410785170A CN 104529786 A CN104529786 A CN 104529786A
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- WQTOEJFFITYKAB-UHFFFAOYSA-N COCCc(cc1N)cc(N)c1N Chemical compound COCCc(cc1N)cc(N)c1N WQTOEJFFITYKAB-UHFFFAOYSA-N 0.000 description 1
- JZYKMKLSGUHYED-UHFFFAOYSA-N Nc(cc(cc1N)-c(cccc2)c2[N+]([O-])=O)c1N Chemical compound Nc(cc(cc1N)-c(cccc2)c2[N+]([O-])=O)c1N JZYKMKLSGUHYED-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N Nc1ccccc1[N+]([O-])=O Chemical compound Nc1ccccc1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- JTLFHJVKSMHCKT-UHFFFAOYSA-N [O-][N+](c(cccc1)c1C(CC1=[F])=CC(F)=C1F)=O Chemical compound [O-][N+](c(cccc1)c1C(CC1=[F])=CC(F)=C1F)=O JTLFHJVKSMHCKT-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention provides a method for synthesizing 3,4,5-trifluoro-2'-nitrobiphenyl; a synthetic route is as shown in the description, wherein -X represents a substituent group selected from one of -Cl, -Br, -I, COOH, -N2Cl and -N2HSO4. The method comprises the following steps of (1), dissolving the raw materials including 3,4,5-trifluorobenzeneboronic acid and ortho-nitro substituted benzene in a solvent, and adding a catalyst and an acid-binding agent; (2), reacting while stirring till finishing; (3), washing, and extracting to obtain an organic phase; and (4), concentrating, and recrystallizing to obtain 3,4,5-trifluoro-2'-nitrobiphenyl. According to the invention, the Ms-Pd catalyst having high catalytic activity is adopted; furthermore, multi-batch indiscriminate use can be realized; and the method is high in yield, high in product purity, convenient to postprocess and environment friendly.
Description
Technical field
The present invention relates to a kind of important intermediate of synthesizing fluorobenzene pyrrole bacterium amine, particularly relate to the synthesis of a kind of functional group biphenol compound, be specially the synthetic method of the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-.
Background technology
Functional group's biphenol compound, due to himself physics, chemical property, by direct or indirect be widely a kind of very important body compound in the synthesis and preparative of medicine and agricultural chemicals, study its synthetic method and the development of association area be significant.
Wherein, the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-, as a kind of functional group biphenol compound, is intermediate important in field of fine chemical, especially can as the synthesis material of sterilant fluorobenzene pyrrole bacterium amine.About the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-: its molecular formula is: C
12h
6f
3nO
2; Chemical name is: the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-; English name is: 3,4,5-Trifluoro-2'-nitrobiphenyl; No. CAS is: 1056196-56-5; Structural formula is:
The preparation method of the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-carries out mainly through linked reaction.Document, report and the data of synthesizing about this intermediate are little, and in actual building-up process, often use that some are special, homemade catalyzer, and for 3,4, the large-scale production application of the fluoro-2 '-nitrobiphenyl of 5-tri-, all contributes without remarkable.Wherein, patent (PCT 2009156359), disclose a kind of with 2,2-dimethyl-1,3-bis-diphenylphosphine propane (CAS:80326-98-3) be raw material, PdCl
2for catalyzer, and under high temperature, high pressure, synthesize the method for above-mentioned biphenol compound, but, described catalyzer, without purchase source, is copying usually because of catalyzer problem in its synthetic method process, the result that can not get, and, synthetic environment needs high temperature, high pressure, so, is difficult to large-scale application in plant produced.
Therefore, for the synthetic method of scale operation that can realize the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-, and can solve the deficiencies in the prior art, be that those skilled in the art expect always, and the difficult problem never solved.
Summary of the invention
In order to solve the defect that prior art exists in actual applications, solve the difficulty that current those skilled in the art not yet capture, realize the scale operation of the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-, the invention provides a kind of 3, the new and effective new synthetic method of the fluoro-2 '-nitrobiphenyl of 4,5-tri-, wherein, the catalytic activity of used catalyst is high, and can realize multiple batches of applying mechanically; Described synthetic method reactions steps is short, operational condition is gentle, spent acid is few.There is the advantages such as synthetic method yield is high, good product purity, convenient post-treatment, raw materials cost are low, environmental protection, there is the prospect of suitability for industrialized production.
The theme of a first aspect of the present invention is the synthetic route of the synthetic method of the fluoro-2 '-nitrobiphenyl of a kind of 3,4,5-tri-, it is characterized in that, for:
Wherein, the substituting group representated by-X is-Cl ,-Br ,-I, COOH ,-N
2cl ,-N
2hSO
4in any one.
According to a kind of preferred embodiment of synthetic route of the present invention, wherein ,-X is preferably-I.
The theme of a second aspect of the present invention is the synthetic method of the fluoro-2 '-nitrobiphenyl of a kind of 3,4,5-tri-, it is characterized in that, comprises
Step 1: raw material 3,4,5-trifluoro-benzene boric acid, adjacent nitro substituted benzene are dissolved in solvent, and add catalyzer and acid binding agent;
Step 2: stirring reaction, to terminating;
Step 3: washing, extracts to obtain organic phase;
Step 4: concentrated, obtains the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-.
A kind of preferred embodiment according to a second aspect of the present invention, in described step 1:
Wherein, described solvent is selected from any one in protic solvent, non-protonic solvent: described protic solvent comprises methyl alcohol, ethanol, propyl alcohol, Virahol, water, formic acid and acetic acid, is preferably methyl alcohol; Described non-protonic solvent comprises DMF, acetone, ethyl acetate, methylene dichloride, ether, tetracol phenixin, toluene, benzene, normal hexane, hexanaphthene, tetrahydrofuran (THF), chloroform, is preferably toluene.
Wherein, described catalyzer is noble metal catalyst, comprises PdCl
2, Pd (PPh
3)
4, Ms-Pd (molecular sieve complex compound), Pd/C, Pd (OAc)
2, Pt/C, PtCl
2, triphenylphosphine carbonyl hydrogenation Rh (I), two (triphenylphosphine) carbonyl rhodium chloride, two (triphenylphosphine) palladium chloride, two (dibenzyl acetyl) palladium, platinum dioxide, triphenylphosphine rhodium chloride, two (1,4-biphenyl phosphine) butyl palladium chloride (II), ruthenium charcoal (Ru/C), four (triphenylphosphine) platinum, any one in ruthenium trichloride, be more preferably Ms-Pd catalyzer.
Further, the preparation method of described Ms-Pd catalyzer, comprising:
Step 1: by PdCl
2join in organic solvent with 4A molecular sieve;
Step 2: stir, to terminating;
Step 3: suction filtration, and filter cake is dried, obtain white powdery solids, be Ms-Pd catalyzer.
Preferably, described 4A molecular sieve is dry through retort furnace, is 80-100 order;
Preferably, described organic solvent comprises any one or a few the mixed solution in acetone, acetonitrile, methyl alcohol;
Preferably, described churning time is at least two days.
Wherein, described acid binding agent is mineral alkali, any one in organic bases: mineral alkali comprise in sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood, lithium hydroxide any one, be more preferably potassium hydroxide; Organic bases comprise in triethylamine, pyridine, sodium methylate, sodium ethylate, TBAH, lithium alkylide, Lithamide any one, be more preferably pyridine.
Wherein, the usage quantity of described catalyzer is the 0.1%-10% of the fluoro-2 '-nitrobiphenyl weight of 3,4,5-tri-, is more preferably 0.5%.
A kind of preferred embodiment according to a second aspect of the present invention, in described step 2:
Wherein, the temperature of described stirring reaction is 0-100 DEG C, is preferably 35-45 DEG C, is more preferably 40 DEG C.
A kind of preferred embodiment according to a second aspect of the present invention, in described step 3:
Wherein, the terminal of described washing is last aqueous pH values of washing is 2-10, is more preferably 3-6.
A kind of preferred embodiment according to a second aspect of the present invention, in described step 4:
The described concentrated mode preferably by underpressure distillation.
The new synthetic method of 3,4,5-tri-fluoro-2 '-nitrobiphenyls of the present invention, owing to have employed technique scheme, has the following advantages and beneficial effect:
The new and effective synthetic method of (1) 3,4,5-tri-fluoro-2 '-nitrobiphenyl, synthesis step is short, simple process, and solvent cost declines obviously;
(2) above-mentioned novel preparation method can realize continuous prodution, and multiple batches of reaction is applied mechanically, and catalyst activity is high, and reaction conditions is gentle, three-waste free discharge, meet the requirement of environmental protection;
(3) technique aftertreatment is simple, and extraction is concentrated, organic solvent is refining can obtain the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-(purity is 97%).
Embodiment
The invention provides the synthetic route of the synthetic method of the fluoro-2 '-nitrobiphenyl of a kind of 3,4,5-tri-, it is characterized in that, for:
Wherein, the substituting group representated by-X is-Cl ,-Br ,-I, COOH ,-N
2cl ,-N
2hSO
4in any one, be preferably-I.
Present invention also offers the synthetic method of the fluoro-2 '-nitrobiphenyl of a kind of 3,4,5-tri-, it is characterized in that, comprising:
Step 1: raw material 3,4,5-trifluoro-benzene boric acid, adjacent nitro substituted benzene are dissolved in solvent, and add catalyzer and acid binding agent;
Step 2: stirring reaction, to terminating;
Step 3: washing, extracts to obtain organic phase;
Step 4: concentrated, recrystallization obtains the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-.
A kind of preferred embodiment according to a second aspect of the present invention, in described step 1:
Wherein, described solvent is selected from any one in protic solvent, non-protonic solvent: described protic solvent comprises methyl alcohol, ethanol, propyl alcohol, Virahol, water, formic acid and acetic acid, is preferably methyl alcohol; Described non-protonic solvent comprises DMF, acetone, ethyl acetate, methylene dichloride, ether, tetracol phenixin, toluene, benzene, normal hexane, hexanaphthene, tetrahydrofuran (THF), chloroform, is preferably toluene.
Wherein, described catalyzer is noble metal catalyst, comprises PdCl
2, Pd (PPh
3)
4, Ms-Pd (molecular sieve complex compound), Pd/C, Pd (OAc)
2, Pt/C, PtCl
2, triphenylphosphine carbonyl hydrogenation Rh (I), two (triphenylphosphine) carbonyl rhodium chloride, two (triphenylphosphine) palladium chloride, two (dibenzyl acetyl) palladium, platinum dioxide, triphenylphosphine rhodium chloride, two (1,4-biphenyl phosphine) butyl palladium chloride (II), ruthenium charcoal (Ru/C), four (triphenylphosphine) platinum, any one in ruthenium trichloride, be more preferably Ms-Pd catalyzer.
Further, the preparation method of described Ms-Pd catalyzer, comprising:
Step 1: by PdCl
2join in organic solvent with 4A molecular sieve;
Step 2: stir, to terminating;
Step 3: suction filtration, and filter cake is dried, obtain white powdery solids, be Ms-Pd catalyzer.
Preferably, described 4A molecular sieve is dry through retort furnace, is 80-100 order;
Preferably, described organic solvent comprises any one or a few the mixed solution in acetone, acetonitrile, methyl alcohol;
Preferably, described churning time is at least two days.
Wherein, described acid binding agent is mineral alkali, any one in organic bases: mineral alkali comprise in sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood, lithium hydroxide any one, be more preferably potassium hydroxide; Organic bases comprise in triethylamine, pyridine, sodium methylate, sodium ethylate, TBAH, lithium alkylide, Lithamide any one, be more preferably pyridine.
Wherein, the usage quantity of described catalyzer is the 0.1%-10% of the fluoro-2 '-nitrobiphenyl weight of 3,4,5-tri-, is more preferably 0.5%.
A kind of preferred embodiment according to a second aspect of the present invention, in described step 2:
Wherein, the temperature of described stirring reaction is 0-100 DEG C, is more preferably 40 DEG C.
Wherein, described reaction terminates to determine preferably by the method for liquid phase tracking raw material.
A kind of preferred embodiment according to a second aspect of the present invention, in described step 3:
Wherein, the terminal of described washing is last aqueous pH values of washing is 2-10, is more preferably 3-6.
A kind of preferred embodiment according to a second aspect of the present invention, in described step 4:
The described concentrated mode preferably by underpressure distillation.
Described recrystallization is preferably normal hexane, and 3,4, the 5-tri-fluoro-2 '-nitrobiphenyls obtained are pale yellow crystals solid, and fusing point 78.1-78.3 DEG C, liquid content is more than or equal to 97%.
Wherein, the fluoro-2 '-nitrobiphenyl analytical data of 3,4,5-tri-:
1h NMR (400MHz, CDCl
3) δ 8.00-8.05 (m, 2H), 7.90-7.75 (m, 1H), 7.67-7.55 (m, 1H), 7.27-7.14 (m, 2H) ppm; 13C NMR (100MHz, CDCl3) δ 151.9,151.0,141.2,139.1,136.5,135.1,129.4,128.5,128.0,124.7,113.8,112.5ppm.
According to the technical scheme of the new synthetic method of 3,4,5-tri-fluoro-2 '-nitrobiphenyls of the present invention, enumerate embodiment to be further explained it and to illustrate, to understand the present invention better.
Embodiment 1---about screening of catalyst
1, synthetic route:
2, synthetic method (carrying out according to shown in table 1):
Step 1: offer 4 reactions, is all dissolved in solvent DMF by raw material 3,4,5-trifluoro-benzene boric acid, o-chloronitrobenzene, adds acid binding agent triethylamine, and add catalyst Pt Cl respectively
2, Pd (OAc)
2, Pd (PPh
3)
4, Ms-Pd, add-on is 0.5%;
Step 2: at 30 DEG C, stirring reaction, after liquid phase tracking raw material reaction completes, stopped reaction;
Step 3: recycling design and catalyzer, crude product is through washing, extracting to obtain organic phase;
Step 4: concentrated, the optimal result that normal hexane recrystallization obtains the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-is 24.0g, pale yellow crystals solid, fusing point 78.1-78.3 DEG C, liquid content 97%.
1H NMR(400MHz,CDCl
3)δ8.00-8.05(m,2H),7.90-7.75(m,1H),7.67-7.55(m,1H),7.27-7.14(m,2H)ppm；13C NMR(100MHz,CDCl3)δ151.9,151.0,141.2,139.1,136.5,135.1,129.4,128.5,128.0,124.7,113.8,112.5ppm。
3, result:
Table 1: the test-results of catalyst screening
| Numbering | Catalyzer | Acid binding agent | Temperature (DEG C) | Solvent | Yield |
| 1 | PtCl 2 | Triethylamine | 30 | DMF | 75％ |
| 2 | Pd(OAc) 2 | Triethylamine | 30 | DMF | 64％ |
| 3 | Pd(PPh 3) 4 | Triethylamine | 30 | DMF | 55％ |
| 4 | Ms-Pd | Triethylamine | 30 | DMF | 88％ |
Embodiment 2---about the screening of-X
1, synthetic route:
2, synthetic method (carrying out according to shown in table 2):
Raw material 3,4,5-trifluoro-benzene boric acid, 3 kinds of adjacent nitro substituted benzenes are dissolved in solvent methanol, and add acid binding agent sodium bicarbonate and catalyst P dCl by step 1: offer 3 reactions respectively
2, add-on is 0.5%;
Step 2: at 40 DEG C, stirring reaction, after liquid phase tracking raw material reaction completes, stopped reaction;
Step 3: recycling design and catalyzer, crude product is through washing, extracting to obtain organic phase;
Step 4: concentrated, obtains the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-.
3, result:
The test-results of table 2:-X screening
| Numbering | -X | Catalyzer | Acid binding agent | Temperature (DEG C) | Solvent | Yield |
| 1 | -Cl | PdCl 2 | Sodium bicarbonate | 40 | Methyl alcohol | 90％ |
| 2 | -Br | PdCl 2 | Sodium bicarbonate | 40 | Methyl alcohol | 94％ |
| 3 | -I | PdCl 2 | Sodium bicarbonate | 40 | Methyl alcohol | 98％ |
Embodiment 3---about the screening of temperature
1, synthetic route:
2, synthetic method (carrying out according to shown in table 3):
Step 1: offer 5 reactions, all raw material 3,4,5-trifluoro-benzene boric acid, o-chloronitrobenzene are dissolved in solvent DMF, and add acid binding agent sodium bicarbonate and catalyzer Ms-Pd, add-on is 0.5%;
Step 2: respectively at 0 DEG C, 20 DEG C, 40 DEG C, 60 DEG C, 80 DEG C, stirring reaction, after liquid phase tracking raw material reaction completes, stopped reaction;
Step 3: recycling design and catalyzer, crude product is through washing, extracting to obtain organic phase;
Step 4: concentrated, obtains the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-.
3, result:
Table 3: the test-results of temperature screening
| Numbering | Temperature (DEG C) | Catalyzer | Acid binding agent | Solvent | Yield |
| 1 | 0 | Ms-Pd | Sodium bicarbonate | DMF | 80％ |
| 2 | 20 | Ms-Pd | Sodium bicarbonate | DMF | 83％ |
| 3 | 40 | Ms-Pd | Sodium bicarbonate | DMF | 88％ |
| 4 | 60 | Ms-Pd | Sodium bicarbonate | DMF | 90％ |
| 5 | 80 | Ms-Pd | Sodium bicarbonate | DMF | 88％ |
Be described in detail specific embodiments of the invention above, but it is just as example, the present invention is not restricted to specific embodiment described above.To those skilled in the art, any equivalent modifications that the present invention is carried out and substituting also all among category of the present invention.Therefore, equalization conversion done without departing from the spirit and scope of the invention and amendment, all should contain within the scope of the invention.
Claims (10)
1. the synthetic method of tri-fluoro-2 '-nitrobiphenyls, is characterized in that,
Its synthetic route is:
Wherein, the substituting group representated by-X is-Cl ,-Br ,-I ,-COOH ,-N
2cl ,-N
2hSO
4in any one;
Its synthesis step comprises:
Step 1: raw material 3,4,5-trifluoro-benzene boric acid, adjacent nitro substituted benzene are dissolved in solvent, and add catalyzer and acid binding agent;
Step 2: stirring reaction, to terminating;
Step 3: washing, extracts to obtain organic phase;
Step 4: concentrated, recrystallization obtains the fluoro-2 '-nitrobiphenyl of 3,4,5-tri-.
2. the synthetic method of 3,4,5-tri-fluoro-2 '-nitrobiphenyls according to claim 1, it is characterized in that, described-X is-I.
3. the synthetic method of 3,4,5-tri-fluoro-2 '-nitrobiphenyls according to claim 1, is characterized in that, the described solvent in described step 1 be selected from protic solvent, non-protonic solvent any one,
Wherein, described protic solvent comprises methyl alcohol, ethanol, propyl alcohol, Virahol, water, formic acid and acetic acid; Wherein, described non-protonic solvent comprises DMF, acetone, ethyl acetate, methylene dichloride, ether, tetracol phenixin, toluene, benzene, normal hexane, hexanaphthene, tetrahydrofuran (THF), chloroform.
4. the synthetic method of 3,4,5-tri-fluoro-2 '-nitrobiphenyls according to claim 3, is characterized in that, described recrystallization adopts hexane solution, and obtain 3,4, the fluoro-2 '-nitrobiphenyl of 5-tri-is pale yellow crystals solid, and fusing point 78.1-78.3 DEG C, liquid content is more than or equal to 97%.
5. the synthetic method of 3,4,5-tri-fluoro-2 '-nitrobiphenyls according to claim 1, it is characterized in that, described catalyzer is noble metal catalyst, comprises PdCl
2, Pd (PPh
3)
4, molecular sieve complex compound Ms-Pd, Pd/C, Pd (OAc)
2, Pt/C, PtCl
2, triphenylphosphine carbonyl hydrogenation Rh, two (triphenylphosphine) carbonyl rhodium chloride, two (triphenylphosphine) palladium chloride, two (dibenzyl acetyl) palladium, platinum dioxide, triphenylphosphine rhodium chloride, two (Isosorbide-5-Nitrae-biphenyl phosphine) butyl palladium chloride, ruthenium charcoal Ru/C, four (triphenylphosphine) platinum, any one in ruthenium trichloride.
6. the synthetic method of 3,4,5-tri-fluoro-2 '-nitrobiphenyls according to claim 5, it is characterized in that, described catalyzer is Ms-Pd catalyzer, and its preparation method comprises:
Step 1: by PdCl
2join in organic solvent with 4A molecular sieve;
Step 2: stir, to terminating;
Step 3: suction filtration, and filter cake is dried, obtain white powdery solids, be Ms-Pd catalyzer;
Wherein, described 4A molecular sieve is dry through retort furnace, is 80-100 order;
Wherein, described organic solvent comprises any one or a few the mixed solution in acetone, acetonitrile, methyl alcohol;
Wherein, described churning time is at least two days.
7. the synthetic method of 3,4,5-tri-fluoro-2 '-nitrobiphenyls according to claim 1, is characterized in that, described acid binding agent is any one in mineral alkali, organic bases:
Wherein, described mineral alkali comprises any one in sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood, lithium hydroxide;
Wherein, described organic bases comprises any one in triethylamine, pyridine, sodium methylate, sodium ethylate, TBAH, lithium alkylide, Lithamide.
8. the synthetic method of 3,4,5-tri-fluoro-2 '-nitrobiphenyls according to claim 1, it is characterized in that, the usage quantity of described catalyzer is the 0.1%-10% of the fluoro-2 '-nitrobiphenyl weight of 3,4,5-tri-.
9. the synthetic method of 3,4,5-tri-fluoro-2 '-nitrobiphenyls according to claim 1, it is characterized in that, the temperature of the described stirring reaction in described step 2 is 35-45 DEG C.
10. the synthetic method of 3,4,5-tri-fluoro-2 '-nitrobiphenyls according to claim 1, is characterized in that, the described washing in described step 3 refer to aqueous pH values be 3-6.
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| CN105399635A (en) * | 2015-12-15 | 2016-03-16 | 上海师范大学 | Microwave synthesis method of 2-nitro-3',4',5'-trifluoro-1,1'-biphenyl |
| CN106518755A (en) * | 2016-09-28 | 2017-03-22 | 江苏中邦制药有限公司 | Method for synthesising 2,3-dichloropyridine |
| CN106986774A (en) * | 2017-05-11 | 2017-07-28 | 蚌埠中实化学技术有限公司 | A kind of preparation method of 2 nitrobiphenyl |
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| CN107382734A (en) * | 2017-07-21 | 2017-11-24 | 南通嘉禾化工有限公司 | The Suzuki coupling reactions of the ammino palladium chtalyst nitro-chlorobenzene of dichloro two |
| CN107488113A (en) * | 2016-06-13 | 2017-12-19 | 上海泰禾国际贸易有限公司 | A kind of method for synthesizing o-aminobiphenyl class compound |
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| CN109956871A (en) * | 2017-12-25 | 2019-07-02 | 浙江省化工研究院有限公司 | A kind of preparation method of the fluoro- 2 '-nitrobiphenyl of 3,4,5- tri- |
| CN111606808A (en) * | 2020-06-09 | 2020-09-01 | 温州大学 | Synthetic method of 3 ', 4', 5 '-trifluoro-2-nitro-1, 1' -biphenyl |
| CN113185404A (en) * | 2021-04-30 | 2021-07-30 | 武汉大学 | 1, 2-biaxial chiral biaryl compound and preparation method and application thereof |
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