CN105315194A - Synthetic method of 2-bromocarbazole and intermediate thereof - Google Patents
Synthetic method of 2-bromocarbazole and intermediate thereof Download PDFInfo
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- CN105315194A CN105315194A CN201410311264.9A CN201410311264A CN105315194A CN 105315194 A CN105315194 A CN 105315194A CN 201410311264 A CN201410311264 A CN 201410311264A CN 105315194 A CN105315194 A CN 105315194A
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- nitrobiphenyl
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- phosphite
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 15
- PJRGCJBBXGNEGD-UHFFFAOYSA-N 2-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Br)C=C3NC2=C1 PJRGCJBBXGNEGD-UHFFFAOYSA-N 0.000 title abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 40
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims abstract description 20
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims abstract description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 12
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 238000006193 diazotization reaction Methods 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 46
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
- 229910052794 bromium Inorganic materials 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- KEURHSDOWCBXFX-UHFFFAOYSA-N 1-(2-bromophenyl)-2-nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=CC=C1Br KEURHSDOWCBXFX-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 238000010828 elution Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000013517 stratification Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- SVAHHCNTAZYUAT-UHFFFAOYSA-N 1-(4-bromophenyl)-2-nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=C(Br)C=C1 SVAHHCNTAZYUAT-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000012414 tert-butyl nitrite Substances 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 4
- PLVCYMZAEQRYHJ-UHFFFAOYSA-N (2-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Br PLVCYMZAEQRYHJ-UHFFFAOYSA-N 0.000 description 3
- YOJKKXRJMXIKSR-UHFFFAOYSA-N 1-nitro-2-phenylbenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=CC=C1 YOJKKXRJMXIKSR-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- JDLGBNVBFOLSMR-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3NC12.[Br] Chemical class C1=CC=CC=2C3=CC=CC=C3NC12.[Br] JDLGBNVBFOLSMR-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Abstract
The invention discloses a synthetic method of 2-bromocarbazole and an intermediate thereof. The synthetic method includes the steps of 1) with dichloromethane as a solvent and tert-butyl nitrite as a diazotization reagent, diazotizating o-nitroaniline and performing a coupling reaction to the diazotizated o-nitroaniline and bromobenzene to prepare an intermediate 4-bromo-2'-nitrobiphenyl; 2) adding enough triethyl phosphite to the 4-bromo-2'-nitrobiphenyl to perform a ring closing reaction to the 4-bromo-2'-nitrobiphenyl and the triethyl phosphite; 3) when the ring closing reaction is finished, adding enough hydrochloric acid to damage the triethyl phosphite which is not reacted; and 4) filtering and drying a reaction product to prepare the 2-bromocarbazole.
Description
Technical field
The present invention relates to organic synthesis method, particularly relate to the synthetic method of a kind of 2-bromine carbazole and intermediate thereof.
Background technology
2-bromine carbazole is a kind of intermediate of very important luminous organic material.In the last few years, the research of organic photoelectrical material was very active, and wherein the derivative of carbazole has good light stability, spectral absorption wide ranges and the high feature of optoelectronic transformation efficiency efficiency, was one of organic photoelectrical material of current focus development research.
The synthetic method that current custom adopts has following two kinds:
Method one, adopt 2 nitro biphenyl synthesis, its reactive chemistry formula is as follows:
The shortcoming of this method is: material 2 nitro biphenyl expensive, when going up bromine in the reaction, use bromine, bromine has extremely strong toxic and corrodibility, when normal temperature, just can volatilize extremely strong strong toxic smog, stimulate the mucous membrane of eyes and respiratory tract, draw tears from sb, energy skin ambustion, produce strong shouting pain not easily to cure, there is very large hazard to person, be unfavorable for HUMAN HEALTH.
Method two, adopt bromobenzeneboronic acid synthesis, its reactive chemistry formula is as follows:
The shortcoming of this method is: bromobenzeneboronic acid is expensive, and expensive palladium catalyst is used in bromobenzeneboronic acid and o-bromonitrobenzene Suzuki coupling in addition, has a large amount of side reaction to generate simultaneously, is difficult to purifying.
Summary of the invention
In order to solve the problems of the prior art, the object of this invention is to provide a kind of not only economy but also the synthetic method of the 2-bromine carbazole of easy handling and intermediate thereof.
For achieving the above object, the present invention is by the following technical solutions: the synthetic method of a kind of 2-bromine carbazole and intermediate thereof comprises the following steps: step one, utilize methylene dichloride (English name dichloromethane, be called for short DCM) be solvent, nitrite tert-butyl is diazo reagent, make o-Nitraniline diazotization and bromobenzene linked reaction, prepare the bromo-2 '-nitrobiphenyl of intermediate 4-; Step 2, abundant triethyl-phosphite is added in the bromo-2 '-nitrobiphenyl of 4-, make the bromo-2 '-nitrobiphenyl of 4-and triethyl-phosphite generation ring closure reaction, after ring closure reaction terminates, add enough hydrochloric acid again and destroy the complete triethyl-phosphite of unreacted, eventually pass filtration, drying, namely obtain 2-bromine carbazole.
Preferred scheme, the process preparing the bromo-2 '-nitrobiphenyl of intermediate 4-in described step one is: first in reaction vessel, add o-Nitraniline, bromobenzene and methylene dichloride, and the temperature in reaction vessel is down to 0 DEG C, slowly the nitroso-group tert-butyl ester is dripped again in reaction vessel, in the process of reacting, control temperature is at 0-5 DEG C, after fully reacting 30 minutes, slowly be warming up to back flow reaction 5 hours again, again to adding enough water in it, stratification, extract dichloromethane layer, with the dichloromethane layer that 10% salt acid elution extracts, extract organic phase again, organic phase is evaporated to dry, in the organic phase after concentrated, add ethanol be warming up to backflow, be cooled to 20 DEG C again, eventually pass filtration, dry, namely the bromo-2 '-nitrobiphenyl of solid 4-of white is obtained.
Preferred scheme further, in described step one, the chemical equation of o-Nitraniline diazotization and bromobenzene linked reaction is:
Further preferred version, in described step 2, the process of the bromo-2 '-nitrobiphenyl of 4-and triethyl-phosphite generation ring closure reaction is: add triethyl-phosphite in the bromo-2 '-nitrobiphenyl of the 4-obtained in step one, be heated to 160 DEG C, after making it react 2 hours, be cooled to 20 DEG C, add concentrated hydrochloric acid again, mixture is heated to back flow reaction 1 hour, then is cooled to 30 DEG C, make it separate out a large amount of solid, eventually pass filtration, drying, namely obtain the 2-bromine carbazole of solid.
In described step 2 the bromo-2 '-nitrobiphenyl of 4-and triethyl-phosphite generation ring closure reaction chemical formula be:
Beneficial effect of the present invention is: utilize o-Nitraniline, bromobenzene, triethyl-phosphite to prepare 2-bromine carbazole and the bromo-2 '-nitrobiphenyl of intermediate 4-thereof, not only economy but also easy handling for raw material, simultaneously few to the pollution of environment, has saved the production cost of enterprise.The reaction earning rate of 2-bromine carbazole and the bromo-2 '-nitrobiphenyl of intermediate 4-thereof is high.
Accompanying drawing explanation
The present invention is further described below in conjunction with the drawings and specific embodiments:
Fig. 1 is HPLC collection of illustrative plates ((HighPerformanceLiquidChromatography, the high performance liquid chromatography of the bromo-2 '-nitrobiphenyl of intermediate 4-prepared by the present invention; Also known as " high pressure liquid chromatography ") schematic diagram;
Fig. 2 is the HPLC collection of illustrative plates schematic diagram of 2-bromine carbazole prepared by the present invention.
Embodiment
Embodiment 1, the synthetic method of a kind of 2-bromine carbazole and intermediate thereof comprises the following steps:
Step one, utilize methylene dichloride (English name dichloromethane is called for short DCM) to be solvent, nitrite tert-butyl is diazo reagent, makes o-Nitraniline diazotization and bromobenzene linked reaction, prepares the bromo-2 '-nitrobiphenyl of intermediate 4-;
Step 2, abundant triethyl-phosphite is added in the bromo-2 '-nitrobiphenyl of 4-, make the bromo-2 '-nitrobiphenyl of 4-and triethyl-phosphite generation ring closure reaction, after ring closure reaction terminates, add enough hydrochloric acid again and destroy the complete triethyl-phosphite of unreacted, eventually pass filtration, drying, namely obtain 2-bromine carbazole.
The detailed step of the present embodiment is as follows:
The synthesis of the bromo-2 '-nitrobiphenyl of intermediate 4-, 138g o-Nitraniline and 188.4g bromobenzene (1.2mol) is added in 2000ml reaction flask, 1000ml methylene dichloride, mixture in reaction flask is cooled to 0 DEG C, the slow dropping 91.5g nitroso-group tert-butyl ester, react heat release, the temperature that we control in reaction flask is reacted 30 minutes at 0-5 DEG C, again the mixture in reaction flask is slowly warming up to the back flow reaction 5 little time, add 500ml water again, stratification, by dichloromethane layer 100ml10% salt acid elution, wherein organic phase is evaporated to dry, add 1000ml ethanol again and be warming up to backflow, finally be cooled to 20 DEG C, through filtering, dry, obtain the bromo-2 '-nitrobiphenyl 202g of solid 4-of white, HPLC collection of illustrative plates (the HighPerformanceLiquidChromatography of 4-bromine 2 '-nitrobiphenyl as shown in Figure 1, high performance liquid chromatography, also known as " high pressure liquid chromatography ") display 4-bromo-2 '-nitrobiphenyl content is that strings 72.6% are received in the bromo-2 '-nitrobiphenyl reaction of 99.38%, 4-.
Obtaining of 2-bromine carbazole, bromo-for the 202g4-obtained in 500g triethyl-phosphite and step one 2 '-nitrobiphenyl is joined in 2000ml reaction flask, be heated to 160 DEG C, after making it react 2 hours, be cooled to 20 DEG C again, add the concentrated hydrochloric acid that 300ml concentration is 35%, mixture in reacting by heating bottle was to back flow reaction 1 hour, again mixture is cooled to about 30 DEG C, now can separate out a large amount of off-white color solids, eventually pass filtration, dry, namely the solid 2-bromine carbazole 136.6g of off-white color is obtained, the HPLC collection of illustrative plates display 2-bromine carbazole content of 2 bromine carbazoles is 99.91% as shown in Figure 2, the reaction yield 67.6% of 2-bromine carbazole.
Claims (5)
1. a synthetic method for 2-bromine carbazole and intermediate thereof, is characterized in that: its synthetic method comprises the following steps:
Step one, utilize methylene dichloride for solvent, nitrite tert-butyl is diazo reagent, makes o-Nitraniline diazotization and bromobenzene linked reaction, prepares the bromo-2 '-nitrobiphenyl of intermediate 4-;
Step 2, abundant triethyl-phosphite is added in the bromo-2 '-nitrobiphenyl of 4-, make the bromo-2 '-nitrobiphenyl of 4-and triethyl-phosphite generation ring closure reaction, after ring closure reaction terminates, add enough hydrochloric acid again and destroy the complete triethyl-phosphite of unreacted, eventually pass filtration, drying, namely obtain 2-bromine carbazole.
2. the synthetic method of a kind of 2-bromine carbazole and intermediate thereof according to claim 1, it is characterized in that: the process preparing the bromo-2 '-nitrobiphenyl of intermediate 4-in described step one is: first in reaction vessel, add o-Nitraniline, bromobenzene and methylene dichloride, and the temperature in reaction vessel is down to 0 DEG C, slowly the nitroso-group tert-butyl ester is dripped again in reaction vessel, in the process of reacting, control temperature is at 0-5 DEG C, after fully reacting 30 minutes, slowly be warming up to back flow reaction 5 hours again, again to adding enough water in it, stratification, extract dichloromethane layer, with the dichloromethane layer that 10% salt acid elution extracts, extract organic phase again, organic phase is evaporated to dry, in the organic phase after concentrated, add ethanol be warming up to backflow, be cooled to 20 DEG C again, eventually pass filtration, dry, namely the bromo-2 '-nitrobiphenyl of solid 4-of white is obtained.
3. the synthetic method of a kind of 2-bromine carbazole and intermediate thereof according to claim 2, is characterized in that: in described step one, the chemical equation of o-Nitraniline diazotization and bromobenzene linked reaction is:
4. the synthetic method of a kind of 2-bromine carbazole and intermediate thereof according to claim 1, it is characterized in that: in described step 2, the process of the bromo-2 '-nitrobiphenyl of 4-and triethyl-phosphite generation ring closure reaction is: in the bromo-2 '-nitrobiphenyl of the 4-obtained in step one, add triethyl-phosphite, be heated to 160 DEG C, after making it react 2 hours, be cooled to 20 DEG C, add concentrated hydrochloric acid again, mixture is heated to back flow reaction 1 hour, be cooled to 30 DEG C again, it is made to separate out a large amount of solid, eventually pass filtration, drying, namely obtain the 2-bromine carbazole of solid.
5. the synthetic method of a kind of 2-bromine carbazole and intermediate thereof according to claim 4, is characterized in that: in described step 2 the bromo-2 '-nitrobiphenyl of 4-and triethyl-phosphite generation ring closure reaction chemical formula be:
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110437134A (en) * | 2019-07-24 | 2019-11-12 | 苏州络森生物科技有限公司 | A kind of synthetic method of 2,7- Dimethylcarbazole |
| CN111307991A (en) * | 2020-04-07 | 2020-06-19 | 中钢集团南京新材料研究院有限公司 | Method for simultaneously detecting bromobenzene and carbazole compounds by adopting high performance liquid chromatography |
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| CN102439019A (en) * | 2009-03-23 | 2012-05-02 | 通用显示公司 | Heteroleptic iridium complex |
| CN103189469A (en) * | 2010-08-27 | 2013-07-03 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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2014
- 2014-07-01 CN CN201410311264.9A patent/CN105315194B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102439019A (en) * | 2009-03-23 | 2012-05-02 | 通用显示公司 | Heteroleptic iridium complex |
| CN103189469A (en) * | 2010-08-27 | 2013-07-03 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
Non-Patent Citations (2)
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| AKE BERGMAN，ET AL.: "Synthesis of 14C-Labelled and Unlabelled Coplanar Polychlorinated Biphenyls (PCBs)", 《ACTA CHEMICA SCANDINAVICA》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110437134A (en) * | 2019-07-24 | 2019-11-12 | 苏州络森生物科技有限公司 | A kind of synthetic method of 2,7- Dimethylcarbazole |
| CN111307991A (en) * | 2020-04-07 | 2020-06-19 | 中钢集团南京新材料研究院有限公司 | Method for simultaneously detecting bromobenzene and carbazole compounds by adopting high performance liquid chromatography |
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Effective date of registration: 20190220 Address after: 201207 China (Shanghai) free trade pilot area, 2277 Chong Lane 1, 506 room. Patentee after: UIV CHEM-YURUI (SHANGHAI) CHEMICAL CO.,LTD. Address before: 450009 No. 24, No. 10 Building, No. 9 Hanghai East Road, Guancheng Hui District, Zhengzhou City, Henan Province Patentee before: Zhao Xiaoyu |
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Denomination of invention: A synthesis method of 2-bromocarbazole and its intermediates Granted publication date: 20181225 Pledgee: Shanghai Pudong Development Bank Co.,Ltd. Jinqiao Sub branch Pledgor: UIV CHEM-YURUI (SHANGHAI) CHEMICAL CO.,LTD. Registration number: Y2024980005748 |