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A method for synthesizing high-purity 3-bromo-n-phenylcarbazole

A phenylcarbazole and high-purity technology, which is applied in the field of organic synthesis of N-phenylcarbazole derivatives, can solve the problems of high reaction risk factor, complicated post-treatment process, difficult industrialized production and the like, and achieves easy control of the reaction. , easy to control the reaction drop rate, easy to control the effect

Active Publication Date: 2022-04-29
SINOSTEEL NANJING NEW MATERIALS RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, bromine simple substance has poor reaction selectivity and low product yield as bromination agent; NBS has high product yield as bromination agent, but there are still deficiencies such as complicated post-treatment and many wastes; KBr / KBrO 3 When used as a bromination reagent, active bromine molecules are generated under the condition of acid (sulfuric acid or acetic acid) as a solvent and then participate in the bromination reaction, but there are disadvantages such as harsh reaction conditions, complicated post-treatment, and low atom utilization.
In particular, the bromination system is KBr / KBrO 3 When, Potassium Bromate and Potassium Bromide are jointly used as the brominating agent of the reaction, that is, the bromine source provider, wherein Potassium Bromate also acts as an oxidizing agent, and KBr reacts first as a reducing agent to generate bromine simple substance to participate in the reaction, and in acidic solvent (sulfuric acid or acetic acid) conditions Lower reaction, high reaction risk factor, complex post-treatment process, difficult to industrialized production

Method used

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  • A method for synthesizing high-purity 3-bromo-n-phenylcarbazole
  • A method for synthesizing high-purity 3-bromo-n-phenylcarbazole
  • A method for synthesizing high-purity 3-bromo-n-phenylcarbazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] At room temperature, add 24.3g of N-phenylcarbazole (99%, 0.10mol) and 50mL of dichloromethane into a 250mL four-necked round-bottomed flask equipped with a stirrer and a thermometer, stir until completely dissolved, and then reduce the reaction System temperature to -10°C; 24.3g hydrobromic acid (40%, 0.12mol, 17.6mL) was added dropwise, and 13.6g hydrogen peroxide (30%, 0.12mol, 12.2 mL), wherein, the dropping rate of the brominating agent is 3.0mL / min, the dropping rate of the oxidizing agent is 0.5mL / min, and the dropping process can strictly control the reaction temperature below -10°C; The reaction was carried out for 6 hours, during which the conversion rate of N-phenylcarbazole detected by the liquid phase reached ≥ 99%, and the reaction was stopped. After the reaction is finished, add quantitative sodium carbonate saturated aqueous solution to the reaction system to adjust the pH of the mixed solution to neutral, wash 3 times with water washing separation metho...

Embodiment 2

[0054] At room temperature, add 243.3g of N-phenylcarbazole (99%, 1.00mol) and 500mL of dichloromethane into a 1000mL four-necked round-bottomed flask equipped with a stirrer and a thermometer, stir until completely dissolved, and then reduce the reaction System temperature to -10°C; 212.4g hydrobromic acid (40%, 1.05mol, 153.9mL) was added dropwise, and 119.0g hydrogen peroxide (30%, 1.05mol, 107.2 mL), wherein, the dropping rate of the brominating agent is 3.0mL / min, the dropping rate of the oxidizing agent is 0.5mL / min, and the dropping process can strictly control the reaction temperature below -10°C; The reaction was carried out for 6 hours, during which the conversion rate of N-phenylcarbazole detected by the liquid phase reached ≥ 99%, and the reaction was stopped. After the reaction is finished, add quantitative sodium carbonate saturated aqueous solution to the reaction system to adjust the pH of the mixed solution to neutral, wash 3 times with water washing and separ...

Embodiment 3

[0056] This example is basically the same as Example 1, except that 40.5g of hydrobromic acid (20%, 0.10mol, 35.0mL) and 17.9g of hydrogen peroxide (20%, 0.105mol, 16.7mL) were added.

[0057] After the end of the reaction in this example, HPLC detected that the conversion rate of N-phenylcarbazole failed to reach 99%, and 24.5 g of 3-bromo-N-phenylcarbazole (the content detected by HPLC was ≥99%) had a yield of 76.0%; In the process of completing the reaction system of hydrobromic acid and hydrogen peroxide, the volume ratio of the inorganic phase to the organic phase is close to 1:1, and the concentration of bromine molecules generated is too low, so that N-phenylcarbazole cannot be completely converted into 3-bromo-N-phenyl Carbazole affects the conversion and yield of the reaction.

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Abstract

The invention discloses a method for synthesizing high-purity 3-bromo-N-phenylcarbazole, which belongs to the technical field of chemistry. The steps are: after dissolving N-phenylcarbazole in the solvent, add brominating agent and oxidizing agent in sequence at a low temperature of -20°C to 10°C, and after the addition is completed, keep the reaction temperature at -20°C to 10°C to react When the conversion rate of N-phenylcarbazole reaches ≥99%, the reaction is stopped, wherein the temperature of the reaction system is kept within 5° C. when the bromination agent and the oxidant are added; Washing, rotary evaporation, recrystallization, and vacuum drying yielded high-purity 3-bromo-N-phenylcarbazole. The oxidative bromination method used in the present invention has the characteristics of high atom utilization rate, low raw material cost, high reaction selectivity, short preparation period, simple preparation operation and easy controllable reaction.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis of N-phenylcarbazole derivatives, and specifically relates to a method for synthesizing 3-bromo-N-phenylcarbazole through oxidative bromination of N-phenylcarbazole. Background technique [0002] Organic Light Emitting Diode (OLED) has excellent characteristics such as low energy consumption, high brightness, fast response, thin thickness, wide viewing angle, all solid state, self-illumination, and flexibility; it can be applied to wider panels Displays and semiconductors have huge market prospects in the fields of solid-state lighting and flat panel displays, and are one of the focus and research hotspots in the scientific research and industry circles. OLED is composed of organic semiconductor materials, light-emitting materials and electrode stacks, and organic electroluminescent materials have the greatest impact on its performance. Organic electroluminescent materials are divided i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 杨修光裴晓东朱叶峰吴忠凯张玲申保金骆艳华
Owner SINOSTEEL NANJING NEW MATERIALS RES INST CO LTD
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