CN114195617A - Synthetic method of 4-bromobiphenyl - Google Patents
Synthetic method of 4-bromobiphenyl Download PDFInfo
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- CN114195617A CN114195617A CN202111639293.4A CN202111639293A CN114195617A CN 114195617 A CN114195617 A CN 114195617A CN 202111639293 A CN202111639293 A CN 202111639293A CN 114195617 A CN114195617 A CN 114195617A
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- bromobiphenyl
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- biphenyl
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- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000010189 synthetic method Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000000047 product Substances 0.000 claims abstract description 16
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 4
- 238000001308 synthesis method Methods 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- 238000004821 distillation Methods 0.000 claims description 21
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 20
- 239000004305 biphenyl Substances 0.000 claims description 20
- 235000010290 biphenyl Nutrition 0.000 claims description 20
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- -1 methyl imidazolium tetrafluoroborate Chemical compound 0.000 claims description 12
- 239000002244 precipitate Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 11
- 229940102001 zinc bromide Drugs 0.000 claims description 10
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000002608 ionic liquid Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000004065 wastewater treatment Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000009423 ventilation Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002826 coolant Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing 4-bromobiphenyl, which sequentially comprises the following steps: (1) mixing and preparing; (2) carrying out oxidation reaction; (3) and (5) separating and distilling. Has the advantages that: the invention provides a synthesis method of 4-bromobiphenyl, which has mild reaction conditions, does not have potential safety hazard, simultaneously does not need to use a large amount of strong acid and strong base, avoids generating a large amount of byproduct salt, and reduces economic cost; meanwhile, the 4-bromobiphenyl product has high yield, high product purity, good quality and simple preparation process.
Description
The technical field is as follows:
the invention relates to a preparation method of 4-bromobiphenyl, in particular to a synthesis method of 4-bromobiphenyl.
Background art:
the 4-bromobiphenyl is a key intermediate of a plurality of fine chemical products such as laser dyes, liquid crystal materials, pesticides, medicines and the like.
The existing method for preparing 4-bromobiphenyl mainly comprises the following two methods:
(1) cooling water, p-bromoaniline and concentrated hydrochloric acid, keeping the temperature at 0-5 ℃, slowly adding sodium nitrite aqueous solution, diazotizing until starch potassium iodide test paper is blue, and filtering out clear diazonium solution. Adding benzene into the diazo solution, stirring at 5-10 deg.C for half an hour, slowly adding dropwise sodium hydroxide solution, stirring for 3 hr, and stirring at room temperature for 45 hr. Separating out a benzene layer, washing with water, distilling out benzene, performing reduced pressure distillation, collecting 170-175 ℃ (1.06kPa) fractions, and recrystallizing with ethanol to obtain a finished product with a melting point of 90 ℃, wherein the actual yield is 86% and the purity is 98%; the following problems exist with the above method: diazotization reaction is carried out in excessive strong acid, a large amount of strong acid and strong base are needed, a large amount of byproduct salt is generated, and economic loss is caused; meanwhile, the reaction is a diazotization reaction, and potential safety hazards exist.
(2) The Chinese invention patent CN200810157467.1 (published as 2009.3.4) reports that 4-bromobiphenyl is prepared by reacting biphenyl, liquid bromine and chlorine under the catalytic condition of a catalyst, the preparation process is complex, the reactant hydrochloric acid is treated, the number of byproducts is large, and the actual yield of the product is only 62%.
The invention content is as follows:
the invention aims to provide a method for synthesizing 4-bromobiphenyl, which has simple process and high product yield.
The purpose of the invention is implemented by the following technical scheme: a method for synthesizing 4-bromobiphenyl sequentially comprises the following steps:
(1) mixing preparation: adding a solvent into a reaction kettle, stirring, adding biphenyl, ionic liquid, zinc bromide and hydrobromic acid during stirring, and introducing nitrogen for 5-10min to replace air in the reaction kettle;
(2) and (3) oxidation reaction: introducing nitric oxide and oxygen into the reaction kettle in the step (1); stopping introducing air for 2-6h, controlling the temperature to be 0-20 ℃ in the air introducing process, preserving the temperature at the temperature for reacting for 1-5 h, and obtaining a reactant after the reaction is finished;
(3) separation and distillation: standing the reactant in the step (2) for 0.5-1h, layering the reactant from top to bottom, sending the upper aqueous phase to wastewater treatment, sending the lower precipitate to a concentration kettle, and distilling at normal pressure until the distillation temperature reaches 80-120 ℃; then carrying out reduced pressure distillation, controlling the vacuum degree to be more than or equal to 0.08mpa and the distillation temperature to be 120-150 ℃ until the solvent is evaporated, and drying the precipitate to obtain the product of 4-bromobiphenyl.
Under the catalytic conditions of ionic liquid, zinc bromide and nitric oxide, the chemical formula of the preparation reaction of 4-bromobiphenyl is as follows:
further, in the step (1), the molar ratio of the biphenyl to the solvent is 1: 5-15, preferably 1: 7.
Further, the solvent is dichloromethane or acetonitrile.
Further, in the step (1), the molar ratio of the biphenyl to the ionic liquid is 1: 0.005-0.01, preferably 1: 0.006.
Further, the ionic liquid is at least one of methyl imidazolium tetrafluoroborate, 1-hexyl-3-methylimidazole tetrafluoroborate, 1-butyl-3-methylimidazole tetrafluoroborate and 1, 3-dimethyl imidazole tetrafluoroborate.
Further, in the step (1), the molar ratio of the biphenyl to the zinc bromide is 1: 0.03-0.1, preferably 1: 0.05.
Further, in the step (1), the molar ratio of the biphenyl to the hydrobromic acid is 1: 1.05-1.3, preferably 1: 1.1.
Further, in the step (1), the flow rate of the introduced nitrogen gas is 1-2L/min.
Further, in the step (2), the molar ratio of the biphenyl to the introduced nitric oxide is 1: 0.1-0.4, preferably 1: 0.2.
Further, in the step (2), the molar ratio of the biphenyl to the introduced oxygen is 1: 0.257-0.35, preferably 1: 0.28.
The invention has the advantages that:
the invention provides a synthesis method of 4-bromobiphenyl, which adopts biphenyl, hydrobromic acid and oxygen as reaction raw materials, takes ionic liquid, zinc bromide and nitric oxide as catalysts, and produces the 4-bromobiphenyl by oxidation, the reaction conditions are mild, no potential safety hazard exists, and simultaneously, a large amount of strong acid and strong base are not needed to be used, thereby avoiding generating a large amount of byproduct salt and reducing the economic cost; meanwhile, the 4-bromobiphenyl product has high yield, high product purity, good quality and simple preparation process.
The specific implementation mode is as follows:
the present invention will be described in further detail by way of examples.
Example 1: adding 462ml (7mol) of dichloromethane into a reaction kettle, adding 154g (1mol) of biphenyl, 1g (0.006mol) of methyl imidazolium tetrafluoroborate, 11.25g (0.05mol) of zinc bromide and 186g (1.1mol) of 48% hydrobromic acid under stirring, introducing 5min of nitrogen with the flow rate of 2L/min to replace air in the reaction kettle after the feeding is finished, cooling to 0-20 ℃ through a cooling medium, starting simultaneously introducing 6g (0.2mol) of nitric oxide and 9g (0.28mol) of oxygen, stopping after 4h of ventilation, controlling the temperature to be 0-20 ℃ in the ventilation process, and preserving the temperature for 3 hours at the temperature; after the heat preservation is finished, standing for 1 hour, separating out a lower layer, removing wastewater from an upper layer of water phase, sending a lower layer of precipitate to a concentration kettle, and distilling at normal pressure until the distillation temperature reaches 80-120 ℃; then carrying out reduced pressure distillation, controlling the vacuum degree to be more than or equal to 0.08mpa and the distillation temperature to be 120-150 ℃ until dichloromethane is evaporated, and drying the precipitate to obtain 220g of 4-bromobiphenyl product, wherein the actual yield is 94.42% (molar yield) and the purity is 99%.
The actual yield of the product 4-bromobiphenyl prepared by the embodiment is obviously higher than that disclosed in application No. CN200810157467.1 entitled "a preparation method of 4-bromobiphenyl", and the product 4-bromobiphenyl prepared by the embodiment has high purity and good quality.
Example 2: adding 660ml (10mol) of dichloromethane into a reaction kettle, adding 154g (1mol) of biphenyl, 1.3g (0.008mol) of methyl imidazolium tetrafluoroborate, 18g (0.008mol) of zinc bromide and 203g (1.2mol) of 48% hydrobromic acid under stirring, introducing nitrogen with the flow rate of 1L/min for 10min to replace air in the reaction kettle after the feeding is finished, cooling to 0-20 ℃ through a cooling medium, starting to simultaneously introduce 9g (0.3mol) of nitric oxide and 11.52g (0.32mol) of oxygen, stopping after 6h of ventilation, controlling the temperature to be 0-20 ℃ in the ventilation process, and preserving the temperature to react for 5 hours at the temperature; after the heat preservation is finished, standing for 1 hour, separating out a lower layer, removing wastewater from an upper layer of water phase, sending a lower layer of precipitate to a concentration kettle, and distilling at normal pressure until the distillation temperature reaches 80-120 ℃; then carrying out reduced pressure distillation, controlling the vacuum degree to be more than or equal to 0.08mpa and the distillation temperature to be 120-150 ℃ until dichloromethane is evaporated, and drying the precipitate to obtain 212g of the product 4-bromobiphenyl, wherein the actual yield is 91% (molar yield) and the purity is 99%.
Example 3: adding 990ml (15mol) of dichloromethane into a reaction kettle, adding 154g (1mol) of biphenyl, 1.7g (0.01mol) of methyl imidazolium tetrafluoroborate, 22.5g (0.1mol) of zinc bromide and 219.8g (1.3mol) of 48% hydrobromic acid under stirring, introducing nitrogen with the flow rate of 1.5L/min for 6min to replace air in the reaction kettle after the feeding is finished, cooling to 0-20 ℃ through a cooling medium, starting simultaneously introducing 12g (0.4mol) of nitric oxide and 12.6g (0.35mol) of oxygen, stopping after 2h of ventilation, controlling the temperature to be 0-20 ℃ in the ventilation process, and preserving the temperature for reaction for 1h at the temperature; after the heat preservation is finished, standing for 1 hour, separating out a lower layer, removing wastewater from an upper layer of water phase, sending a lower layer of precipitate to a concentration kettle, and distilling at normal pressure until the distillation temperature reaches 80-120 ℃; then carrying out reduced pressure distillation, controlling the vacuum degree to be more than or equal to 0.08mpa and the distillation temperature to be 120-150 ℃ until dichloromethane is evaporated, and drying the precipitate to obtain 209.7g of the product, namely the 4-bromobiphenyl, wherein the actual yield is 90 percent (molar yield) and the purity is 99 percent.
Example 4: adding 330ml (5mol) of dichloromethane into a reaction kettle, adding 154g (1mol) of biphenyl, 0.85g (0.005mol) of methyl imidazolium tetrafluoroborate, 6.75g (0.03mol) of zinc bromide and 177.5g (1.05mol) of 48% hydrobromic acid under stirring, introducing nitrogen with the flow rate of 1.5L/min for 6min after the feeding is finished to replace the air in the reaction kettle, cooling to 0-20 ℃ through a cooling medium, starting simultaneously introducing 3g (0.1mol) of nitric oxide and 9.25g (0.257mol) of oxygen, stopping after 2h of ventilation, controlling the temperature to be 0-20 ℃ in the ventilation process, and preserving the temperature for reaction for 1h at the temperature; after the heat preservation is finished, standing for 1 hour, separating out a lower layer, removing wastewater from an upper layer of water phase, sending a lower layer of precipitate to a concentration kettle, and distilling at normal pressure until the distillation temperature reaches 80-120 ℃; then carrying out reduced pressure distillation, controlling the vacuum degree to be more than or equal to 0.08mpa and the distillation temperature to be 120-150 ℃ until dichloromethane is evaporated, and drying the precipitate to obtain 205g of the product 4-bromobiphenyl, wherein the actual yield is 88 percent (molar yield) and the purity is 99 percent.
The foregoing is a preferred embodiment of the present invention, and it will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the principles of the invention, and such modifications and adaptations are intended to be included within the scope of the invention.
Claims (10)
1. The synthesis method of 4-bromobiphenyl is characterized by comprising the following steps in sequence:
(1) mixing preparation: adding a solvent into a reaction kettle, stirring, adding biphenyl, ionic liquid, zinc bromide and hydrobromic acid during stirring, and introducing nitrogen for 5-10min to replace air in the reaction kettle;
(2) and (3) oxidation reaction: introducing nitric oxide and oxygen into the reaction kettle in the step (1); stopping introducing air for 2-6h, controlling the temperature to be 0-20 ℃ in the air introducing process, preserving the temperature at the temperature for reacting for 1-5 h, and obtaining a reactant after the reaction is finished;
(3) separation and distillation: standing the reactant in the step (2) for 0.5-1h, layering the reactant from top to bottom, sending the upper aqueous phase to wastewater treatment, sending the lower precipitate to a concentration kettle, and distilling at normal pressure until the distillation temperature reaches 80-120 ℃; then carrying out reduced pressure distillation, controlling the vacuum degree to be more than or equal to 0.08mpa and the distillation temperature to be 120-150 ℃ until the solvent is evaporated, and drying the precipitate to obtain the product of 4-bromobiphenyl.
2. The method for synthesizing 4-bromobiphenyl as claimed in claim 1, wherein in step (1), the molar ratio of the biphenyl to the solvent is 1: 5-15.
3. The method for synthesizing 4-bromobiphenyl according to claim 2, wherein the solvent is dichloromethane or acetonitrile.
4. The method for synthesizing 4-bromobiphenyl as claimed in claim 1, wherein in step (1), the molar ratio of the biphenyl to the ionic liquid is 1: 0.005-0.01.
5. The method for synthesizing 4-bromobiphenyl according to claim 4, wherein the ionic liquid is at least one of methyl imidazolium tetrafluoroborate, 1-hexyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium tetrafluoroborate and 1, 3-dimethylimidazolium tetrafluoroborate.
6. The method for synthesizing 4-bromobiphenyl as claimed in claim 1, wherein in step (1), the molar ratio of the biphenyl to the zinc bromide is 1: 0.03-0.1.
7. The method for synthesizing 4-bromobiphenyl as claimed in claim 1, wherein in step (1), the molar ratio of the biphenyl to the hydrobromic acid is 1: 1.05-1.3.
8. The method for synthesizing 4-bromobiphenyl as claimed in claim 1, wherein in the step (1), the flow rate of the introduced nitrogen gas is 1-2L/min.
9. The method for synthesizing 4-bromobiphenyl as claimed in claim 1, wherein in the step (2), the molar ratio of the biphenyl to the introduced nitric oxide is 1: 0.1-0.4.
10. The method for synthesizing 4-bromobiphenyl as claimed in claim 1, wherein in the step (2), the molar ratio of the biphenyl charged to the oxygen fed is 1: 0.257-0.35.
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| CN202111639293.4A CN114195617B (en) | 2021-12-29 | 2021-12-29 | Synthesis method of 4-bromodiphenyl |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004307461A (en) * | 2003-02-18 | 2004-11-04 | Sumitomo Chem Co Ltd | Method for producing biaryl compound |
| CN101376619A (en) * | 2008-10-08 | 2009-03-04 | 山东海王化工股份有限公司 | Preparation of 4-bromobiphenyl |
| CN112441900A (en) * | 2019-09-05 | 2021-03-05 | 浙江中科创越药业有限公司 | Preparation method of 4-biphenylacetic acid |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004307461A (en) * | 2003-02-18 | 2004-11-04 | Sumitomo Chem Co Ltd | Method for producing biaryl compound |
| CN101376619A (en) * | 2008-10-08 | 2009-03-04 | 山东海王化工股份有限公司 | Preparation of 4-bromobiphenyl |
| CN112441900A (en) * | 2019-09-05 | 2021-03-05 | 浙江中科创越药业有限公司 | Preparation method of 4-biphenylacetic acid |
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