CN-122010658-A - Synthetic method of deuterated 1-naphthyl-9-anthracene-D9

Abstract

The invention belongs to the technical field of deuterated organic chemical synthesis, and particularly relates to a synthetic method of deuterated 1-naphthyl-9-anthracene-D9, which comprises the following steps of taking 1-naphthyl boric acid and deuterated 9-bromoanthracene as raw materials, and carrying out Suzuki coupling reaction on Pd (PPh 3 ) 4 or Pd (PPh 3 ) 2 Cl 2 ) serving as a catalyst in a potassium phosphate alkaline environment at 50-80 ℃ to prepare deuterated 1-naphthyl-9-anthracene-D9..

Inventors

• AN JINCHENG
• ZHANG NING
• JIA KE
• CHEN HUAN
• GUO JINGWEI
• WANG XUEPENG
• WANG YANAN
• WANG SHUANGCHAO
• SHUANG LI
• Cheng Jiafan

Assignees

• 派瑞科技有限公司

Dates

Publication Date

20260512

Application Date

20251230

Claims (6)

1. 1. A method for synthesizing deuterated 1-naphthyl-9-anthracene-D9, which is characterized by comprising the following steps: Taking 1-naphthyl boric acid and deuterated 9-bromoanthracene as raw materials, and carrying out Suzuki coupling reaction on Pd (PPh 3 ) 4 or Pd (PPh 3 ) 2 Cl 2 ) serving as a catalyst in a potassium phosphate alkaline environment at 50-80 ℃ to prepare deuterated 1-naphthyl-9-anthracene-D9.
2. 2. The method for synthesizing deuterated 1-naphthyl-9-anthracene-D9 according to claim 1, wherein the reaction time is 4-8 hours.
3. 3. The method for synthesizing deuterated 1-naphthyl-9-anthracene-D9 according to claim 1 or 2, wherein the solvent for the reaction is a mixed solvent of 1, 4-dioxane and water in a volume ratio of 5-7:1.
4. 4. The method for synthesizing deuterated 1-naphthyl-9-anthracene-D9 according to claim 1 or 2, wherein the mass ratio of the 1-naphthyl boric acid to the deuterated 9-bromoanthracene to the potassium phosphate is 1:1-2:1.8-3.2.
5. 5. The method for synthesizing deuterated 1-naphthyl-9-anthracene-D9 according to claim 1 or 2, wherein the catalyst is used in an amount of 0.1% -1% of the deuterated 9-bromoanthracene molar amount.
6. 6. The method for synthesizing deuterated 1-naphthyl-9-anthracene-D9 according to claim 1 or 2, further comprising the step of purifying the deuterated 1-naphthyl-9-anthracene-D9 obtained by the reaction: And cooling the reaction system after the reaction to room temperature, adding deionized water to precipitate solid, filtering, drying, and recrystallizing toluene to obtain the deuterated 1-naphthyl-9-anthracene-D9 pure product.

Description

Synthetic method of deuterated 1-naphthyl-9-anthracene-D9 Technical Field The invention belongs to the technical field of deuterated organic chemical synthesis, and particularly relates to a synthetic method of deuterated 1-naphthyl-9-anthracene-D9. Background The existing 1-naphthyl-9-anthracene synthesis method generally adopts a Suzuki coupling reaction, takes 1-naphthyl boric acid and 9-bromoanthracene as raw materials, carries out coupling under the catalysis of palladium catalysts (such as Pd (PPh 3)4 or Pd (PPh 3)2Cl2)), uses potassium carbonate as a base and reacts at a high temperature (100 ℃), however, when the method is applied to the synthesis of deuterated 9-bromoanthracene, the deuteration rate of the palladium catalysts is obviously reduced due to the hydrogen-deuterium exchange effect, and the quality of target products is affected. Disclosure of Invention Aiming at the defects of the prior art, the invention provides a synthetic method of deuterated 1-naphthyl-9-anthracene-D9, which realizes the preparation of a target product with high deuteration rate and high yield in the presence of a palladium catalyst. Specifically, the invention provides the following technical scheme: A synthetic method of deuterated 1-naphthyl-9-anthracene-D9, which comprises the following steps: Taking 1-naphthyl boric acid and deuterated 9-bromoanthracene as raw materials, and carrying out Suzuki coupling reaction on Pd (PPh 3)4 or Pd (PPh 3)2Cl2) serving as a catalyst in a potassium phosphate alkaline environment at 50-80 ℃ to prepare deuterated 1-naphthyl-9-anthracene-D9. The reaction formula is as follows: preferably, the reaction time is 4 to 8 hours. Preferably, the solvent for the reaction is a mixed solvent of 1, 4-dioxane and water in a volume ratio of 5-7:1. Preferably, the mass ratio of the 1-naphthyl boric acid to the deuterated 9-bromoanthracene to the potassium phosphate is 1:1-2:1.8-3.2, and more preferably 1:1-2:3-3.2. Preferably, the catalyst is used in an amount of 0.1% -1% of the molar amount of deuterated 9-bromoanthracene. Preferably, the method further comprises the step of purifying the deuterated 1-naphthyl-9-anthracene-D9 prepared by the reaction: And cooling the reaction system after the reaction to room temperature, adding deionized water to precipitate solid, filtering, drying, and recrystallizing toluene to obtain the deuterated 1-naphthyl-9-anthracene-D9 pure product. The invention has the advantages that: 1) According to the synthetic method of deuterated 1-naphthyl-9-anthracene-D9, provided by the invention, under the condition of using a palladium catalyst, the high deuteration rate is still maintained; 2) The synthetic method of deuterated 1-naphthyl-9-anthracene-D9 provided by the invention has the advantages that the yield of the prepared deuterated 1-naphthyl-9-anthracene-D9 pure product is more than 84%, the deuteration rate is more than 97.5%, the purity is more than 99.3%, and the high yield, the high deuteration rate and the high purity are simultaneously considered; 3) According to the synthetic method of the deuterated 1-naphthyl-9-anthracene-D9, provided by the invention, the deuteration rate of the product is further improved to be more than 98.5% by optimizing the raw material proportion. Drawings FIG. 1 is a mass spectrum of deuterated 1-naphthyl-9-anthracene-D9 prepared in example 1; FIG. 2 is a liquid phase diagram of deuterated 1-naphthyl-9-anthracene-D9 prepared in example 1; FIG. 3 is a nuclear magnetic resonance spectrum of deuterated 1-naphthyl-9-anthracene-D9 prepared in example 1. Detailed Description For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention, which are used for illustrating the present invention but are not intended to limit the scope of the present invention. The specific techniques or conditions are not identified in the examples and are described in the literature in this field or are carried out in accordance with the product specifications. In the following examples, deuterated 9-bromoanthracene was used from Ningbo-extract chemical technology Co. Example 1 300ML of 1, 4-dioxane, 52g of potassium phosphate, 17g of 1-naphthalene boric acid, 25g of deuterated 9-bromoanthracene and 50mL of water are sequentially added into a 500mL three-necked round bottom flask equipped with a thermometer and a spherical condenser, nitrogen bubbling is carried out for 20min, and 1g of tetra-triphenylphosphine palladium (Pd (PPh) 4) catalyst is added under the protection of nitrogen. Regulating the temperature of an oil bath kettle to 70 ℃, reacting for 6 hours at the temperature of 65 ℃ in a round bottom flask, stopping the reaction, naturally cooling to room temperature, introducing