CN113582966A - 2-bromodibenzo [1,4] dioxane compound, preparation method and application - Google Patents
2-bromodibenzo [1,4] dioxane compound, preparation method and application Download PDFInfo
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- CN113582966A CN113582966A CN202110860132.1A CN202110860132A CN113582966A CN 113582966 A CN113582966 A CN 113582966A CN 202110860132 A CN202110860132 A CN 202110860132A CN 113582966 A CN113582966 A CN 113582966A
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- bromodibenzo
- dioxane
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- -1 2-bromodibenzo [1,4] dioxane compound Chemical class 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 27
- GSUCEGNAROQSGU-UHFFFAOYSA-N 2-bromodibenzo-p-dioxin Chemical compound C1=CC=C2OC3=CC(Br)=CC=C3OC2=C1 GSUCEGNAROQSGU-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 16
- YMQPKONILWWJQG-UHFFFAOYSA-N 4-bromo-1,2-difluorobenzene Chemical compound FC1=CC=C(Br)C=C1F YMQPKONILWWJQG-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006798 ring closing metathesis reaction Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000012065 filter cake Substances 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims 1
- 238000009776 industrial production Methods 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000000463 material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- GIUGGRUEPHPVNR-UHFFFAOYSA-N 2-chlorodibenzo-p-dioxin Chemical compound C1=CC=C2OC3=CC(Cl)=CC=C3OC2=C1 GIUGGRUEPHPVNR-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 230000003321 amplification Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- SISAYUDTHCIGLM-UHFFFAOYSA-N bromine dioxide Inorganic materials O=Br=O SISAYUDTHCIGLM-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000003199 nucleic acid amplification method Methods 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CXHXFDQEFKFYQJ-UHFFFAOYSA-N 2-bromo-4-chloro-1-iodobenzene Chemical compound ClC1=CC=C(I)C(Br)=C1 CXHXFDQEFKFYQJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BBOLNFYSRZVALD-UHFFFAOYSA-N 1,2-diiodobenzene Chemical compound IC1=CC=CC=C1I BBOLNFYSRZVALD-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/24—[b,e]-condensed with two six-membered rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a 2-bromodibenzo [1,4] dioxane compound, a preparation method and application thereof, relating to the technical field of organic synthesis, wherein the preparation method comprises the following steps: the method comprises the following steps: 3, 4-difluorobromobenzene and catechol are taken as raw materials, and under the alkaline condition, 2-bromodibenzo [1,4] dioxane is prepared by ring closure. The method provided by the invention has the advantages of easily available raw materials, efficient and safe preparation process, simple operation and suitability for industrial production.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a 2-bromodibenzo [1,4] dioxane compound, and a preparation method and application thereof.
Background
The 2-bromodibenzo [1,4] dioxane contains bromine, has high reaction activity, can realize the expansion of a molecular structure by introducing other molecular fragments through reactions such as Suzuki, Still, Buchwald-Hartwig, Heck, Miyaura and the like, and shows excellent application in the reactions. Derivatives synthesized by using the above-mentioned reaction 2-bromodibenzo [1,4] dioxane as an intermediate are widely used for synthesis of materials having a conjugated structure, and have wide applications in the fields of field effect transistors, organic light emitting diodes, and the like.
At present, the reported synthetic methods of 2-bromodibenzo [1,4] dioxane are basically prepared in two steps. Dibenzo [1,4] dioxane is prepared by using o-halophenol as a raw material (method 1: o-chlorophenol as a raw material, Russian Chemical Bulletin,67(10),1903, 1907; 2018, method 2: o-bromophenol as a raw material, RSC Advances,4(83), 44105-44116; 2014) and catechol as raw materials (method 3: catechol and o-diiodobenzene as raw materials, Tetrahedron,70(6), 1125-1132; 2014, method 4: catechol and o-dinitrobenzene as raw materials, WO 2013110135 Al), and then preparing 2-bromodibenzo [1,4] dioxane by bromine bromination (method 4: CN109776490A, method 5: Chemosphere,16(8-9), 1661-6; 1987).
In the first step of preparation, the o-halophenol in the methods 1 and 2 is a reactant and a reaction solvent, the stirring is extremely difficult during the preparation, the reaction temperature is high, great risk exists during the amplification production, the yield of the method 1 is low (45%), the expensive material Pd used in the method 2 is high, and the production cost is high. The yield in method 3 was too low (18%) and was not suitable for scale-up preparation. In method 4, the cost of o-dinitrobenzene in the current market is relatively high, the raw material is difficult to purchase, and the reaction yield is low (method 4: 41%). In the second step of preparation, bromine is used for bromination, so that the environmental pollution is great, the operation safety is lower, and the removal of polybrominated compounds is difficult in the post-treatment purification. So that the whole route is poor in realizability.
The preparation route is as follows:
the first step preparation route:
the second step of the preparation route:
in addition, in the preparation of 2-chlorodibenzo [1,4] dioxane, which is a 2-bromodibenzo [1,4] dioxane family compound reported at present, 2-chlorodibenzo [1,4] dioxane is prepared by using catechol and 2-bromo-4-chloroiodobenzene as raw materials and catalyzing the raw materials by copper powder (patent US 20180013076).
In the method, the using amount of copper powder is large (50% equivalent), the density of the copper powder is large, and a reaction system is difficult to stir uniformly and the reaction is insufficient during the amplification preparation. And a large amount of copper-containing wastewater can be generated during the post-treatment, the environmental pollution is large, the operation is complex, and great risk exists during the amplification production. And the raw material 2-bromo-4-chloroiodobenzene has higher production cost and lower yield (70%) on the basis of higher market price, fewer suppliers and unstable supply.
In addition, when the 2-chlorodibenzo [1,4] dioxane structure is used for introducing other molecular fragments to realize the expansion of the molecular structure through reactions such as Suzuki, Still, Heck, Miyaura, Buchwald-Hartwig and the like, compared with the 2-bromodibenzo [1,4] dioxane structure, the activity (halogen activity: -I > -Br > -Cl in the reaction) is poor, and no obvious advantage is generated.
The preparation route is as follows:
disclosure of Invention
In order to solve the problems, the invention provides a 2-bromodibenzo [1,4] dioxane compound and a preparation method thereof, and the method adopts easily available raw materials, has high efficiency and safety in the synthesis process, is simple to operate and is suitable for industrial production.
The invention aims to provide a preparation method of a 2-bromodibenzo [1,4] dioxane compound, which comprises the following steps:
3, 4-difluorobromobenzene and catechol are taken as raw materials, and under the alkaline condition, 2-bromodibenzo [1,4] dioxane is prepared by ring closure.
More preferably, the method specifically comprises the following steps:
under the protection of inert gas or nitrogen, 3, 4-difluorobromobenzene and catechol are mixed, then reaction solvents of N-methyl pyrrolidone and an acid-binding agent are sequentially added, nucleophilic substitution reaction is carried out for 3-4 h at 155-160 ℃, and after-treatment, the 2-bromodibenzo [1,4] dioxane is obtained.
More preferably, the molar ratio of the 3, 4-difluorobromobenzene to the catechol is 1: 1.0-1.2.
More preferably, the ratio of the 3, 4-difluorobromobenzene to the N-methylpyrrolidone is 1 g: 5-10 ml.
More preferably, the acid scavenger is potassium carbonate.
More preferably, the molar ratio of the 3, 4-difluorobromobenzene to the potassium carbonate is 1: 1.0-2.5.
More preferably, the post-treatment is to add a certain amount of aqueous solvent into the reaction system, mix the mixture evenly, filter the mixture to obtain a filter cake, wash the filter cake to neutrality, and dry the filter cake to obtain the 2-bromodibenzo [1,4] dioxane.
The second purpose of the invention is to provide a 2-bromodibenzo [1,4] dioxane compound.
The third purpose of the invention is to provide the application of the 2-bromodibenzo [1,4] dioxane compound in an organic light-emitting diode.
Compared with the prior art, the invention has the beneficial effects that:
the invention provides a preparation method of a 2-bromodibenzo [1,4] dioxane compound, which comprises the step of preparing 2-bromodibenzo [1,4] dioxane by ring closure of 3, 4-difluorobromobenzene and catechol under an alkaline condition. Compared with the existing 2-bromodibenzo [1,4] dioxane synthesis method, the method has the advantages of cheap and easily-obtained raw materials, simple operation, less three-waste discharge, safety, convenience, environmental protection in preparation and the like, and is mainly convenient for industrial production.
Drawings
FIG. 1 is a GC-MS spectrum of 2-bromodibenzo [1,4] dioxane as provided in example 1.
Detailed Description
In order to make the technical solutions of the present invention better understood and enable those skilled in the art to practice the present invention, the following embodiments are further described, but the present invention is not limited to the following embodiments.
The experimental methods and the detection methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1
An industrial production method of a 2-bromodibenzo [1,4] dioxane compound specifically comprises the following steps:
under nitrogen protection, N-methylpyrrolidone was added to a 250mL three-necked round bottom flask in the following order: 110mL, 3, 4-difluorobromobenzene: 38.60g (0.20mol), catechol: 22.02g (0.20mol), Potassium carbonate: 66.34g (0.48mol), heating the system to 160 +/-5 ℃, carrying out heat preservation reaction for 4h, cooling to room temperature, adding 1100ml of water, stirring for 10min, filtering, washing a filter cake to be neutral, and drying the material to constant weight to obtain 41.57g of light gray solid with the yield of 79.00 percent. GC-MS calcd for C12H7BrO2(M+) 262, 262; found,262. see FIG. 1, further illustrates that the product prepared in this example is 2-bromodibenzo [1,4]]Dioxane.
The synthetic route is as follows:
example 2
An industrial production method of a 2-bromodibenzo [1,4] dioxane compound specifically comprises the following steps:
under the protection of argon, N-methylpyrrolidone is added into a 250mL three-neck round-bottom flask in sequence: 110mL, 3, 4-difluorobromobenzene: 38.60g (0.20mol), catechol: 26.43g (0.24mol), Potassium carbonate: 66.34g (0.48mol), heating the system to 160 +/-5 ℃, carrying out heat preservation reaction for 4h, cooling to room temperature, adding 1100ml of water, stirring for 10min, filtering, washing a filter cake to be neutral, and drying the material to constant weight to obtain 43.55g of light gray solid with yield of 82.76%. GC-MS calcd for C12H7BrO2(M+),262；found,262.
Example 3
An industrial production method of a 2-bromodibenzo [1,4] dioxane compound specifically comprises the following steps:
under the protection of nitrogen, sequentially adding N-methylpyrrolidone into a 1L three-neck round-bottom flask: 551mL, 3, 4-difluorobromobenzene: 192.99g (1mol), catechol: 110.11g (1mol), Potassium carbonate: 165.85g (1.2mol), heating the system to 160 +/-5 ℃, carrying out heat preservation reaction for 7h, cooling to room temperature, adding 5510ml of water, stirring for 10min, filtering, washing a filter cake to be neutral, and drying the material to constant weight to obtain 218.28g of light gray solid with the yield of 82.97%. GC-MS calcd for C12H7BrO2(M+),262；found,262.
It will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, it is intended that such changes and modifications be included within the scope of the appended claims and their equivalents.
Claims (9)
1. A method for preparing a 2-bromodibenzo [1,4] dioxane compound, comprising the steps of:
3, 4-difluorobromobenzene and catechol are taken as raw materials, and under the alkaline condition, 2-bromodibenzo [1,4] dioxane is prepared by ring closure.
2. The method for producing a 2-bromodibenzo [1,4] dioxane compound according to claim 1, comprising the steps of:
under the protection of inert gas or nitrogen, 3, 4-difluorobromobenzene and catechol are mixed, then reaction solvents of N-methyl pyrrolidone and an acid-binding agent are sequentially added, nucleophilic substitution reaction is carried out for 3-4 h at 155-160 ℃, and after-treatment, the 2-bromodibenzo [1,4] dioxane is obtained.
3. The method for preparing a 2-bromodibenzo [1,4] dioxane compound according to claim 2, wherein the molar ratio of 3, 4-difluorobromobenzene to catechol is 1: 1.0-1.2.
4. The method for producing a 2-bromodibenzo [1,4] dioxane compound according to claim 2, wherein the 3, 4-difluorobromobenzene and N-methylpyrrolidone are used in a ratio of 1 g: 5-10 ml.
5. The method for preparing a 2-bromodibenzo [1,4] dioxane compound according to claim 2, wherein the acid-binding agent is potassium carbonate.
6. The method for preparing a 2-bromodibenzo [1,4] dioxane compound according to claim 5, wherein the molar ratio of the 3, 4-difluorobromobenzene to the potassium carbonate is 1: 1.0-2.5.
7. The method for preparing a 2-bromodibenzo [1,4] dioxane compound according to claim 2, wherein the post-treatment comprises adding a certain amount of aqueous solvent to the reaction system, mixing uniformly, filtering to obtain a filter cake, washing the filter cake to neutrality with water, and drying to obtain the 2-bromodibenzo [1,4] dioxane.
8. The 2-bromodibenzo [1,4] dioxane compound prepared by the preparation method according to any one of claims 1 to 7.
9. Use of the 2-bromodibenzo [1,4] dioxane compound of claim 8 in an organic light emitting diode.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110740998A (en) * | 2017-11-30 | 2020-01-31 | 株式会社Lg化学 | Compound and organic light emitting device including the same |
| CN110741002A (en) * | 2017-10-18 | 2020-01-31 | 株式会社Lg化学 | Novel heterocyclic compounds and organic light-emitting devices containing the same |
| WO2021080334A1 (en) * | 2019-10-23 | 2021-04-29 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
| JP2021086978A (en) * | 2019-11-29 | 2021-06-03 | 学校法人関西学院 | Organic electroluminescent element |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110741002A (en) * | 2017-10-18 | 2020-01-31 | 株式会社Lg化学 | Novel heterocyclic compounds and organic light-emitting devices containing the same |
| CN110740998A (en) * | 2017-11-30 | 2020-01-31 | 株式会社Lg化学 | Compound and organic light emitting device including the same |
| WO2021080334A1 (en) * | 2019-10-23 | 2021-04-29 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
| JP2021086978A (en) * | 2019-11-29 | 2021-06-03 | 学校法人関西学院 | Organic electroluminescent element |
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