A kind of synthetic method of 9-bromoanthracene

Abstract

The present invention discloses a method for synthesizing 9-bromoanthracene. Anthracene and potassium bromide are used as raw materials. The final product, 9-bromoanthracene, is obtained by reacting anthracene and potassium bromide in the presence of ferric chloride and 1-acetoxy-1,2-benzidoxyl-3-(1H)-ketone. The method has the advantages of being inexpensive and readily available, easy to produce, and readily purifiable, and can be developed into an industrialized production method.

Description

Technical Field

[0001] The present invention relates to the technical field of organic synthesis, and in particular to a method for synthesizing 9-bromoanthracene. Background Art

[0002] 9-Bromoanthracene is a key intermediate frequently used in drug development, chemical engineering, and optoelectronic materials. Currently, there are few reported synthetic methods for 9-bromoanthracene, and these methods suffer from expensive raw materials, harsh reaction conditions, and complex processing, making them unsuitable for industrial production.

[0003] Therefore, developing a new synthesis method for 9-bromoanthracene is of great significance for realizing the industrial production of 9-bromoanthracene. Summary of the Invention

[0004] The technical problem solved by the present invention is to provide a method for synthesizing 9-bromoanthracene. The method of the present invention has the advantages of cheap and readily available raw materials, convenient production, environmental protection, safety, and easy purification.

[0005] To solve the above technical problems, the present invention adopts the following technical solution: a synthesis method of 9-bromoanthracene, the reaction formula of the synthesis method is:

[0006]

[0007] The synthesis method comprises the steps of:

[0008] Under an inert gas environment and in carbon tetrachloride, anthracene reacts with potassium bromide in the presence of ferric chloride and 1-acetoxy-1,2-benzidoyl-3-(1H)-one to prepare the final product 9-bromoanthracene.

[0009] As an embodiment of the present invention, the molar equivalent ratio of anthracene to potassium bromide, ferric chloride, and 1-acetyl-1,2-benzidoxyl-3-(1H)-one is 1:(2-3):(2-5):(1-2).

[0010] Preferably, the molar equivalent ratio of anthracene to potassium bromide, ferric chloride, and 1-acetyl-1,2-benzidoxyl-3-(1H)-one is 1:2.5:2.5:1.2.

[0011] As an embodiment of the present invention, the reaction temperature is 50-80°C.

[0012] Preferably, the reaction temperature is 70-80°C.

[0013] As an embodiment of the present invention, the inert gas is nitrogen.

[0014] The present invention provides a novel method for synthesizing 9-bromoanthracene, using inexpensive and readily available anthracene and potassium bromide as raw materials. The final product, 9-bromoanthracene, is obtained through a one-step reaction involving the action of ferric chloride and 1-acetoxy-1,2-benzidoyl-3-(1H)-one. This method has the advantages of inexpensive and readily available raw materials, convenient production, and ease of purification, and can be developed into an industrialized production method. DETAILED DESCRIPTION

[0015] The technical solution of the present invention is described in detail below through examples.

[0016] Example 1

[0017] This embodiment provides a method for synthesizing 9-bromoanthracene, comprising the following steps:

[0018] Under a nitrogen atmosphere, 1.78g of anthracene was added to a three-necked flask, followed by 10ml of carbon tetrachloride. Under nitrogen protection, the temperature of the reaction system was lowered to 0 degrees, and then 2.96g of potassium bromide and 4.05g of ferric chloride were added in batches while stirring, followed by 3.67g of 1-acetoxy-1,2-benzidoyl-3-(1H)-one, controlling the temperature of the system not to exceed 5 degrees. After the addition, the mixture was stirred at 5 degrees for 1 hour, then slowly heated to room temperature, stirred for 30 minutes, and then slowly heated to 78 degrees and reacted for 6 hours. TLC monitored the reaction and the reaction was complete. The reaction solution was then cooled to room temperature and quenched by adding saturated ammonium chloride aqueous solution. The reaction was extracted with dichloromethane and then washed with water. The organic phase was dried and spin-dried, and then passed through a column to obtain 2.1g of 9-bromoanthracene product with a yield of 81.7%. The nuclear magnetic resonance of 9-bromoanthracene is: 1 H NMR (CDCl3): 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).

[0019] During the research process, the following experiments were also conducted. The preparation steps were referred to Example 1, and different reagent amounts and temperatures were selected, as shown in Table 1 below.

[0020] Table 1

[0021]

[0022] The above descriptions are merely embodiments of the present invention and are not intended to limit the patent scope of the present invention. Any equivalent transformations made using the contents of the present invention specification, or any direct or indirect application in other related technical fields, are included in the patent protection scope of the present invention.

Claims

1. A method for synthesizing 9-bromoanthracene, characterized in that: The reaction formula of the synthesis method is: The synthesis method comprises the steps of: Under an inert gas environment, in carbon tetrachloride, anthracene reacts with potassium bromide in the presence of ferric chloride and 1-acetoxy-1,2-benzidoyl-3-(1H)-one to produce the final product, 9-bromoanthracene. The molar equivalent ratio of anthracene to potassium bromide, ferric chloride, and 1-acetyl-1,2-benzidoxyl-3-(1H)-one is 1:(2-3):(2-5):(1-2).

2. The synthesis method according to claim 1, wherein The molar equivalent ratio of the anthracene to potassium bromide, ferric chloride, and 1-acetyl-1,2-benzidoyl-3-(1H)-one is 1:2.5:2.5:1.

2.

3. The synthesis method according to claim 1, wherein The reaction temperature is 50-80°C.

4. The synthesis method according to claim 3, characterized in that The reaction temperature is 70-80°C.

5. The synthesis method according to claim 1, characterized in that The inert gas is nitrogen.

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