CN114920622B - Technological method for preparing pentafluorobromide benzene - Google Patents
Technological method for preparing pentafluorobromide benzene Download PDFInfo
- Publication number
- CN114920622B CN114920622B CN202210154859.2A CN202210154859A CN114920622B CN 114920622 B CN114920622 B CN 114920622B CN 202210154859 A CN202210154859 A CN 202210154859A CN 114920622 B CN114920622 B CN 114920622B
- Authority
- CN
- China
- Prior art keywords
- reaction
- benzene
- pentafluorobromide
- crude product
- temperature
- 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.)
- Active
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title claims abstract description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000012043 crude product Substances 0.000 claims abstract description 29
- MENYRYNFSIBDQN-UHFFFAOYSA-N 5,5-dibromoimidazolidine-2,4-dione Chemical compound BrC1(Br)NC(=O)NC1=O MENYRYNFSIBDQN-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000012074 organic phase Substances 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 11
- WACNXHCZHTVBJM-UHFFFAOYSA-N 1,2,3,4,5-pentafluorobenzene Chemical compound FC1=CC(F)=C(F)C(F)=C1F WACNXHCZHTVBJM-UHFFFAOYSA-N 0.000 claims description 10
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 6
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 6
- 229960001763 zinc sulfate Drugs 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 2
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052794 bromium Inorganic materials 0.000 abstract description 8
- 238000003912 environmental pollution Methods 0.000 abstract description 3
- 239000012847 fine chemical Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 abstract description 3
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005893 bromination reaction Methods 0.000 description 4
- 239000012190 activator Substances 0.000 description 3
- XEKTVXADUPBFOA-UHFFFAOYSA-N 1-bromo-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Br)C(F)=C1F XEKTVXADUPBFOA-UHFFFAOYSA-N 0.000 description 2
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 2
- MEXUTNIFSHFQRG-UHFFFAOYSA-N 6,7,12,13-tetrahydro-5h-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one Chemical compound C12=C3C=CC=C[C]3NC2=C2NC3=CC=C[CH]C3=C2C2=C1C(=O)NC2 MEXUTNIFSHFQRG-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 239000004153 Potassium bromate Substances 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- XHVUVQAANZKEKF-UHFFFAOYSA-N bromine pentafluoride Chemical compound FBr(F)(F)(F)F XHVUVQAANZKEKF-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a process method for preparing pentafluorobromide benzene, and belongs to the technical field of fine chemical engineering. The dibromohydantoin is activated in sulfuric acid to bromine the p-pentafluorobenzene to obtain the pentafluorobrominated benzene. The yield of the crude product of the process reaches more than 97 percent, the yield after rectification reaches 95 percent, and the purity is more than 99 percent. The technical scheme of the process has the remarkable characteristics of high yield and small environmental pollution, and has better economic value in preparing the products of the pentafluorobromide benzene.
Description
Technical Field
The invention relates to a process method for preparing pentafluorobromide benzene, belonging to the technical field of fine chemical engineering.
Background
Pentafluorobromobenzene is a fine chemical intermediate with wide application, and is mainly used in the fields of medicines and new materials. Six synthetic methods for preparing pentafluorobromide benzene are reported in the literature.
The reaction of pentafluorobenzene with bromine under the catalysis of lewis acid is a classical method for preparing pentafluorobenzene. However, bromine leaks liquid bromine in the transportation and use processes, so that serious personal injury accidents are caused. And bromine is easy to volatilize in the reaction process, so that the utilization rate is not high.
CN102531832 reports that the bromination reaction using potassium bromate and sulfuric acid as bromine sources produces pentafluorobromide benzene in a yield of only 34%.
CN109438168 reports the preparation of pentafluorobromide benzene by bromination reaction under lewis acid catalysis using bromine chloride as a bromine source. The boiling point of bromine chloride is only 10 ℃, and the process operation difficulty is far greater than that of bromine. In addition, the process introduces impurities of the pentafluorobenzene.
CN104529698 reports the reaction of pentafluorophenol with phosphorus tribromide to produce pentafluorobromide benzene. Both pentafluorophenol and phosphorus tribromide are expensive raw materials and this route has no cost advantage.
CN111004089 reports that pentafluorobromine is synthesized in one step by using pentafluorobenzoic acid as a raw material, and the brominating reagent can be bromine, NBS, dibromohydantoin and other brominating reagents. The process has the remarkable advantage of synthesizing the pentafluorobromide benzene from the pentafluorobenzoic acid by one step, and reports that the highest yield is 91%, but 5 times of organic solvent DMF is used, and simultaneously more expensive materials such as pyridine and the like are also used.
Disclosure of Invention
The invention aims to provide a technical method for preparing pentafluorobromide benzene with high yield, which has the remarkable characteristics of high yield and high purity. The dibromohydantoin is adopted to be activated in sulfuric acid to carry out bromination on the pentafluorophenyl to obtain the pentafluorobrominated phenyl. The yield of the crude product of the process reaches more than 97 percent, the yield after rectification reaches 95 percent, and the purity is more than 99 percent. The technical scheme of the process has the remarkable characteristics of high yield and small environmental pollution, and has better economic value in preparing the products of the pentafluorobromide benzene.
The invention discloses a process method for preparing pentafluorobromide benzene, which comprises the following steps:
mixing pentafluorobenzene with concentrated sulfuric acid, controlling the temperature to be 20-40 ℃ and adding an inorganic metal salt activator; adding dibromohydantoin in batches at 20-50 ℃ after the addition; after the addition, controlling the temperature to be 40-80 ℃ to react until the residual content of the pentafluorobenzene is less than 1.0%; after the reaction is finished, cooling and adding the reaction liquid into water, wherein the whole process is not more than 50 ℃; standing for layering, and separating out an organic phase; washing with water to obtain crude product, and rectifying to obtain pentafluorobromide benzene.
Further, in the technical scheme, sulfuric acid is used as a reaction medium in the bromination reaction, and the mixing mass ratio of the pentafluorobenzene to the sulfuric acid is 1:0.5-10; the concentration of sulfuric acid is more than 95%.
Further, in the above technical solution, the activator is selected from zinc sulfate or iron sulfate; the molar ratio of the pentafluorobromide benzene to the activator is 1:0.001-1.
Further, in the above technical scheme, the molar ratio of pentafluorobromobenzene to dibromohydantoin is 1:0.45 to 5.0.
Further, in the technical scheme, after the reaction is finished, the temperature is reduced to 30 ℃, the reaction solution is poured into water, and the temperature of the materials is controlled to be less than 50 ℃.
Further, in the technical scheme, the organic phase is firstly adjusted to be neutral by adopting alkali liquor, and then is washed by water; the yield of the obtained crude product is more than 97%.
Further, in the above technical scheme, the alkaline solution is selected from sodium carbonate, sodium bicarbonate or sodium hydroxide solution; preferably 10% sodium hydroxide solution.
Further, in the technical scheme, the crude product obtained after water washing is purified by a rectifying column to obtain the pentafluorobenzene with the purity of more than 99 percent.
Advantageous effects of the invention
The invention aims to provide a technical method for preparing pentafluorobromide benzene. The yield of the pentafluorobromide benzene prepared by the method can reach more than 95 percent, and the purity can reach more than 99 percent. The technical scheme of the invention has the remarkable characteristics of high yield and small environmental pollution, and has better economic value in preparing the pentafluorobromide benzene product.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
The technical solutions in the embodiments of the present invention will be clearly and completely described below in connection with the embodiments of the present invention. It will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
100 grams of pentafluorophenyl was mixed with 200 grams of sulfuric acid with stirring, and 1.0 grams of zinc sulfate was added below 40 ℃. 91.9 g of dibromohydantoin are added in batches between 20 and 30 ℃. After dibromohydantoin is added, the reaction is carried out for 10 hours at the temperature of 30-40 ℃. When the starting material remained below 1.0% was regarded as the end point of the reaction. After the reaction, the temperature was lowered to 30 ℃. The reaction solution was poured into water during which the temperature of the material did not exceed 50 ℃. Standing for layering, and separating out an organic phase. The organic phase is washed with water to obtain crude product, and the yield of the crude product is 97%. The crude product is rectified to obtain the pentafluorobromide benzene with 92 percent of yield and 99.7 percent of purity.
Example 2
100 grams of pentafluorophenyl was mixed with 200 grams of sulfuric acid with stirring, and 1.2 grams of ferric sulfate was added below 40 ℃. 91.9 g of dibromohydantoin are added in batches between 20 and 30 ℃. After dibromohydantoin is added, the reaction is carried out for 10 hours at the temperature of 30-40 ℃. When the starting material remained below 1.0% was regarded as the end point of the reaction. After the reaction, the temperature was lowered to 30 ℃. The reaction solution was poured into water during which the temperature of the material did not exceed 50 ℃. Standing for layering, and separating out an organic phase. The organic phase is washed with water to obtain crude product, and the yield of the crude product is 96%. The crude product is rectified to obtain the pentafluorobromide benzene with the yield of 91 percent and the purity of 99.5 percent.
Example 3
100 grams of pentafluorophenyl was mixed with 400 grams of sulfuric acid with stirring, and 1.2 grams of zinc sulfate was added below 40 ℃. 136 g of dibromohydantoin are added in batches between 20 and 30 ℃. After dibromohydantoin is added, the reaction is carried out for 4 hours at the temperature of 30-40 ℃. When the starting material remained below 1.0% was regarded as the end point of the reaction. After the reaction, the temperature was lowered to 30 ℃. The reaction solution was poured into water during which the temperature of the material did not exceed 50 ℃. Standing for layering, and separating out an organic phase. The organic phase is washed with water to obtain crude product, and the yield of the crude product is 98%. The crude product is rectified to obtain the pentafluorobromide benzene with the yield of 93 percent and the purity of 99.3 percent.
Example 4
100 grams of pentafluorophenyl was mixed with 300 grams of sulfuric acid with stirring, and 3.6 grams of zinc sulfate was added below 40 ℃. 91.9 g of dibromohydantoin are added in batches between 20 and 30 ℃. After dibromohydantoin is added, the reaction is carried out for 5 hours at the temperature of 60-80 ℃. When the starting material remained below 1.0% was regarded as the end point of the reaction. After the reaction, the temperature was reduced to 50 ℃. The reaction solution was poured into water during which the temperature of the material did not exceed 50 ℃. Standing for layering, and separating out an organic phase. The organic phase is washed with water to obtain crude product, and the yield of the crude product is 96%. The crude product is rectified to obtain the pentafluorobromide benzene with the yield of 91 percent and the purity of 99.6 percent.
Example 5
100 grams of pentafluorophenyl was mixed with 200 grams of sulfuric acid with stirring, and 0.9 grams of ferrous sulfate was added below 40 ℃. 91.9 g of dibromohydantoin are added in batches between 20 and 30 ℃. After dibromohydantoin is added, the reaction is carried out for 10 hours at the temperature of 30-40 ℃. When the starting material remained below 1.0% was regarded as the end point of the reaction. After the reaction is finished, the temperature is reduced to below 30 ℃. The reaction solution was poured into water during which the temperature of the material did not exceed 50 ℃. Standing for layering, and separating out an organic phase. The organic phase is washed with water to obtain crude product, and the yield of the crude product is 93%. The crude product is rectified to obtain the pentafluorobromide benzene with the yield of 87 percent and the purity of 99.5 percent.
The foregoing embodiments illustrate the basic principles, principal features and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the above-described embodiments, and that the above-described embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made without departing from the scope of the principles of the invention, which are defined in the appended claims.
Claims (3)
1. The technological method for preparing pentafluorobromide benzene is characterized by comprising the following steps of: 100 g of pentafluorobenzene and 200 g of sulfuric acid are stirred and mixed, and 1.0 g of zinc sulfate is added below 40 ℃; adding 91.9 g of dibromohydantoin in batches at a temperature of between 20 and 30 ℃; after dibromohydantoin is added, controlling the temperature to be 30-40 ℃ for reaction for 10 hours; when the residual content of the raw materials is less than 1.0%, the reaction is regarded as the end point; after the reaction is finished, cooling to 30 ℃; pouring the reaction solution into water, wherein the temperature of the materials is not more than 50 ℃; standing for layering, and separating out an organic phase; washing the organic phase with water to obtain a crude product, wherein the yield of the crude product is 97%; the crude product is rectified to obtain the pentafluorobromide benzene with 92 percent of yield and 99.7 percent of purity.
2. The technological method for preparing pentafluorobromide benzene is characterized by comprising the following steps of: 100 g of pentafluorobenzene and 200 g of sulfuric acid are stirred and mixed, and 1.2 g of ferric sulfate is added below 40 ℃; adding 91.9 g of dibromohydantoin in batches at a temperature of between 20 and 30 ℃; after dibromohydantoin is added, controlling the temperature to be 30-40 ℃ for reaction for 10 hours; when the residual content of the raw materials is less than 1.0%, the reaction is regarded as the end point; after the reaction is finished, cooling to 30 ℃; pouring the reaction solution into water, wherein the temperature of the materials is not more than 50 ℃; standing for layering, and separating out an organic phase; washing the organic phase with water to obtain a crude product, wherein the yield of the crude product is 96%; the crude product is rectified to obtain the pentafluorobromide benzene with the yield of 91 percent and the purity of 99.5 percent.
3. The technological method for preparing pentafluorobromide benzene is characterized by comprising the following steps of: 100 g of pentafluorobenzene and 300 g of sulfuric acid are stirred and mixed, and 3.6 g of zinc sulfate is added below 40 ℃; adding 91.9 g of dibromohydantoin in batches at a temperature of between 20 and 30 ℃; after dibromohydantoin is added, controlling the temperature to be 60-80 ℃ for reaction for 5 hours; when the residual content of the raw materials is less than 1.0%, the reaction is regarded as the end point; after the reaction is finished, cooling to 50 ℃; pouring the reaction solution into water, wherein the temperature of the materials is not more than 50 ℃; standing for layering, and separating out an organic phase; washing the organic phase with water to obtain a crude product, wherein the yield of the crude product is 96%; the crude product is rectified to obtain the pentafluorobromide benzene with the yield of 91 percent and the purity of 99.6 percent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210154859.2A CN114920622B (en) | 2022-02-19 | 2022-02-19 | Technological method for preparing pentafluorobromide benzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210154859.2A CN114920622B (en) | 2022-02-19 | 2022-02-19 | Technological method for preparing pentafluorobromide benzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114920622A CN114920622A (en) | 2022-08-19 |
| CN114920622B true CN114920622B (en) | 2024-04-05 |
Family
ID=82805502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210154859.2A Active CN114920622B (en) | 2022-02-19 | 2022-02-19 | Technological method for preparing pentafluorobromide benzene |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114920622B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0665120A (en) * | 1992-08-12 | 1994-03-08 | Seimi Chem Co Ltd | Production of bromopentafluorobenzene |
| CN101759597A (en) * | 2009-12-31 | 2010-06-30 | 上海康鹏化学有限公司 | Preparation method of 2-trifluoromethyl-4-aminobenzonitrile |
| CN109438168A (en) * | 2018-11-13 | 2019-03-08 | 大连奇凯医药科技有限公司 | The preparation method of five bromofluorobenzenes |
-
2022
- 2022-02-19 CN CN202210154859.2A patent/CN114920622B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0665120A (en) * | 1992-08-12 | 1994-03-08 | Seimi Chem Co Ltd | Production of bromopentafluorobenzene |
| CN101759597A (en) * | 2009-12-31 | 2010-06-30 | 上海康鹏化学有限公司 | Preparation method of 2-trifluoromethyl-4-aminobenzonitrile |
| CN109438168A (en) * | 2018-11-13 | 2019-03-08 | 大连奇凯医药科技有限公司 | The preparation method of five bromofluorobenzenes |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114920622A (en) | 2022-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103373949A (en) | Preparation method of N-phenylmaleimide (PMI) | |
| CN102633696A (en) | Method and technology for preparing p-substituted alkyl benzene sulfonyl chloride by two-step synthesis | |
| CN108715574A (en) | A method of synthesis '-biphenyl diphenol | |
| CN104387322A (en) | Preparation method for caprolactam with low byproducts of ammonium sulfate | |
| CN111548291B (en) | Environment-friendly synthetic method of scorch retarder N-phenyl-N-trichloromethylthio benzenesulfonamide | |
| CN111018693A (en) | 2-methyl-3-methoxybenzoic acid and preparation method thereof | |
| US11981616B2 (en) | Method for preparing 3,3′-diaminobenzidine | |
| CN108191674A (en) | A kind of synthetic method of benzidine compound | |
| CN102952043B (en) | Synthesis method of tert-butyl acrylamide sulfonate | |
| CN114920622B (en) | Technological method for preparing pentafluorobromide benzene | |
| CN106565429B (en) | A kind of preparation method of meta-methoxy phenol | |
| CN107162894A (en) | The post-treatment new process of the chlorobenzoic acid of 5 bromine 2 | |
| CN114539103B (en) | Synthesis method of 2-difluoroethoxy-6-trifluoromethylbenzenesulfonyl chloride | |
| CN107337576B (en) | Normal temperature catalytic synthesis of 2-bromo-5-fluorobenzotrifluoride | |
| CN1359897A (en) | Process for synthesizing hydrate of calcium phenolsulfonate | |
| CN104230764A (en) | Preparation method of 2-acrylamide-2-methyl propanesulfonic acid | |
| CN111004089B (en) | Method for preparing bromopentafluorobenzene from pentafluorobenzoic acid in one step | |
| CN109020915B (en) | Method for improving nitration selectivity of 1, 2-diazoxynaphthalene-4-sulfonic acid | |
| CN108689821B (en) | Method for regenerating chloranil by oxidizing hydrogen peroxide | |
| CN110590702B (en) | Novel method for preparing 2-mercaptobenzothiazole | |
| CN107759626A (en) | A kind of method that inorganic reducing agent reduction prepares 4 AA | |
| CN110683949B (en) | Method for preparing 9, 10-phenanthrene dicarboxylic ester compound | |
| CN115108891B (en) | Preparation method of 3, 5-difluorophenol | |
| CN107721832A (en) | A kind of preparation method of the fluorobenzene ether of 4 chlorine 3 | |
| CN108752180B (en) | Method for preparing 1-chloroanthraquinone by direct chlorination of photocatalytic chlorine |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |