CN115872832A - Synthesis method of 9-bromoanthracene - Google Patents
Synthesis method of 9-bromoanthracene Download PDFInfo
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- CN115872832A CN115872832A CN202211689419.3A CN202211689419A CN115872832A CN 115872832 A CN115872832 A CN 115872832A CN 202211689419 A CN202211689419 A CN 202211689419A CN 115872832 A CN115872832 A CN 115872832A
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- bromoanthracene
- synthesis
- acetoxy
- anthracene
- synthesis method
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- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention discloses a synthesis method of 9-bromoanthracene, which adopts anthracene and potassium bromide as raw materials, and obtains a final product, namely 9-bromoanthracene by one-step reaction under the action of ferric trichloride and 1-acetoxy-1,2-phenyliodoacyl-3- (1H) -ketone. The method has the advantages of cheap and easily obtained raw materials, convenient production and easy purification, and can be developed into an industrial production method.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a synthesis method of 9-bromoanthracene.
Background
9-bromoanthracene is a key intermediate often used in drug research and development, chemical engineering and photoelectric materials. At present, few reports are made on a 9-bromoanthracene synthesis method, and the problems of expensive raw materials, harsh reaction conditions, complex treatment and the like exist, so that the requirement of industrial production cannot be met.
Therefore, the development of a new synthesis method of 9-bromoanthracene has important significance for realizing the industrial production of 9-bromoanthracene.
Disclosure of Invention
The invention solves the technical problem of providing a synthesis method of 9-bromoanthracene, and the method has the advantages of cheap and easily obtained raw materials, convenient production, environmental protection, safety and easy purification.
In order to solve the technical problems, the invention adopts the following technical scheme: a synthesis method of 9-bromoanthracene, which has a reaction formula as follows:
the synthesis method comprises the following steps:
in an inert gas environment, in carbon tetrachloride, anthracene and potassium bromide react under the action of ferric trichloride and 1-acetoxy-1,2-phenyliodoacyl-3- (1H) -ketone to prepare the final product, namely 9-bromoanthracene.
As an embodiment of the invention, the molar equivalent ratio of anthracene to potassium bromide, ferric chloride, 1-acetoxy-1,2-benziodol-3- (1H) -one =1: (2-3): (2-5): (1-2).
Preferably, the molar equivalent ratio of anthracene to potassium bromide, ferric chloride, 1-acetoxy-1,2-phenyliodoxy-3- (1H) -one =1:2.5:2.5:1.2.
as an embodiment of the present invention, the reaction temperature is 50 to 80 ℃.
Preferably, the reaction temperature is 70-80 ℃.
As an embodiment of the invention, the inert gas is nitrogen.
The invention has the beneficial effects that: the invention provides a novel synthesis method of 9-bromoanthracene, which adopts cheap and easily obtained anthracene and potassium bromide as raw materials, and obtains a final product of 9-bromoanthracene through one-step reaction under the action of ferric trichloride and 1-acetoxy-1,2-phenyliodoyl-3- (1H) -ketone. The method has the advantages of cheap and easily obtained raw materials, convenient production and easy purification, and can be developed into an industrial production method.
Detailed Description
The technical solution of the present invention will be described in detail by examples.
Example 1
The embodiment provides a synthesis method of 9-bromoanthracene, which comprises the following steps:
under the nitrogen atmosphere, 1.78g of anthracene is added into a three-mouth bottle, then 10 ml of carbon tetrachloride is added, under the protection of nitrogen, the temperature of a reaction system is reduced to 0 ℃, then 2.96g of potassium bromide and 4.05g of ferric chloride are added in batches while stirring, then 3.67g of 1-acetoxy-1,2-phenyliodoxy-3- (1H) -ketone is added in batches, and the temperature of the system is controlled not to exceed 5 ℃. After the addition, the mixture was stirred at 5 ℃ for 1 hour, then slowly warmed to room temperature, stirred for 30 minutes, and then slowly warmed to 78 ℃ for reaction for 6 hours. TLC monitoring of the reactionAnd (3) completely reacting, cooling the reaction solution to room temperature, adding saturated ammonium chloride aqueous solution to quench the reaction, extracting with dichloromethane, washing with water, drying the organic phase, and passing through a column to obtain 2.1g of a 9-bromoanthracene product with the yield of 81.7%. Nuclear magnetism of 9-bromoanthracene is: 1 H NMR(CDCl 3 ):δ8.63-8.60(m,2H),8.42(s,1H),8.01-7.94(m,2H),7.62-7.58(m,2H),7.55-7.50(m,2H)。
during the study, the following experiments were also carried out, the preparation steps being variously selected with reference to example 1, the amounts of reagents and temperatures, as shown in table 1 below.
TABLE 1
The above description is only an example of the present invention, and is not intended to limit the scope of the present invention, and all equivalent modifications made by the present invention in the specification, or other related fields, which are directly or indirectly applicable to the present invention, are included in the scope of the present invention.
Claims (6)
1. A synthesis method of 9-bromoanthracene is characterized in that the reaction formula of the synthesis method is as follows:
the synthesis method comprises the following steps:
in an inert gas environment, in carbon tetrachloride, anthracene and potassium bromide react under the action of ferric trichloride and 1-acetoxy-1,2-phenyliodoacyl-3- (1H) -ketone to prepare the final product, namely 9-bromoanthracene.
2. The method of synthesis of claim 1, wherein the molar equivalent ratio of anthracene to potassium bromide, ferric chloride, 1-acetoxy-1,2-phenyliodoxy-3- (1H) -one =1: (2-3): (2-5): (1-2).
3. The method of synthesis of claim 2, wherein the molar equivalent ratio of anthracene to potassium bromide, ferric chloride, 1-acetoxy-1,2-phenyliodoxy-3- (1H) -one =1:2.5:2.5:1.2.
4. the synthesis process according to claim 1, characterized in that the reaction temperature is between 50 and 80 ℃.
5. The synthesis process according to claim 4, characterized in that the reaction temperature is 70-80 ℃.
6. The method of synthesis according to claim 1, wherein the inert gas is nitrogen.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211689419.3A CN115872832A (en) | 2022-12-27 | 2022-12-27 | Synthesis method of 9-bromoanthracene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211689419.3A CN115872832A (en) | 2022-12-27 | 2022-12-27 | Synthesis method of 9-bromoanthracene |
Publications (1)
| Publication Number | Publication Date |
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| CN115872832A true CN115872832A (en) | 2023-03-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CN202211689419.3A Pending CN115872832A (en) | 2022-12-27 | 2022-12-27 | Synthesis method of 9-bromoanthracene |
Country Status (1)
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| CN (1) | CN115872832A (en) |
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2022
- 2022-12-27 CN CN202211689419.3A patent/CN115872832A/en active Pending
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