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Synthetic method of 2-Bromo-9-fluorenone

A synthesis method and technology of fluorenone are applied in the field of synthesis of 2-bromo-9-fluorenone, can solve problems such as unfavorable reaction operation, high toxicity, easy leakage, etc., achieve simple and safe operation, high reaction yield, improved selective effect

Active Publication Date: 2015-07-15
HENAN BUSINESS SCI RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] 2-Bromo-9-fluorenone is an important intermediate for the preparation of fluorene series derivatives. Both CN101514161 and CN101148402 have proposed a method for synthesizing 2-bromo-9-fluorenone from 9-fluorenone and elemental bromine, but elemental bromine It is volatile and highly toxic, which is not conducive to the reaction operation, and it is prone to leakage and pollutes the environment

Method used

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  • Synthetic method of 2-Bromo-9-fluorenone

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Experimental program
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Effect test

Embodiment 1

[0024] The synthetic method of 2-bromo-9-fluorenone comprises the following steps:

[0025] 1) Mix 9-fluorenone (20 mmol), phase transfer catalyst (0.6 mmol tetrabutylammonium chloride) and ammonium bromide aqueous solution (40

[0026] wt%, 40 mmol ammonium bromide) and mix and heat the system temperature to 40°C, add 20 mmol potassium bromate three times within 1 hour, the weight ratio of the three additions is 1:2:1, maintain the system temperature and continue the reaction for 5 hours, the reaction temperature is 40°C, the molar ratio of 9-fluorenone, ammonium bromide, and potassium bromate is 1:2:1; the molar ratio of 9-fluorenone to tetrabutylammonium chloride (phase transfer catalyst) is 1:0.03;

[0027] 2) After the reaction, cool down to room temperature, add 10% sodium thiosulfate aqueous solution (bromine removal solution), filter, wash the filter cake with water and dry to obtain 2-bromo-9-fluorenone as a yellow solid with a yield of 96.2 %.

Embodiment 2

[0029] The synthetic method of 2-bromo-9-fluorenone comprises the following steps:

[0030] 1) Mix 9-fluorenone (10 mmol), phase transfer catalyst (2 mmol dodecyltrimethylammonium chloride) and ammonium bromide water

[0031] The solution (20 wt %, 40 mmol ammonium bromide) was mixed and the temperature of the system was heated to 95°C, and 11.5 mmol potassium bromate was added three times within 0.5 h, the weight ratio of the three additions was 1:4:1, and the system temperature was maintained to continue the reaction for 1.5 h, where the molar ratio of 9-fluorenone, ammonium bromide, and potassium bromate is 1:4:1.15; the molar ratio of 9-fluorenone to dodecyltrimethylammonium chloride (phase transfer catalyst) is 1:0.2 ;

[0032] 2) After the reaction, cool down to room temperature, add 15% sodium bisulfite aqueous solution (bromine removal solution), filter, wash the filter cake with water and dry to obtain 2-bromo-9-fluorenone as a yellow solid with a yield of 96.8 %. ...

Embodiment 3

[0034] The synthetic method of 2-bromo-9-fluorenone comprises the following steps:

[0035] 1) Mix 9-fluorenone (10 mmol), phase transfer catalyst (1.5 mmol tetradecyltrimethylammonium chloride) and ammonium bromide aqueous solution (30 wt %, 25 mmol ammonium bromide) and heat the system temperature To 75°C, add 11 mmol potassium bromate three times within 1 hour, the weight ratio of the three additions is 1:3:1, maintain the system temperature and continue the reaction for 3 hours, in which the molar ratio of 9-fluorenone, ammonium bromide, and potassium bromate is 1:2.5 : 1.1; the molar ratio of 9-fluorenone to tetradecyltrimethylammonium chloride (phase transfer catalyst) is 1:0.15;

[0036] 2) After the reaction, cool down to room temperature, add 20% sodium sulfite aqueous solution (bromine removal solution), filter and wash the filter cake with water

[0037] After drying, 2-bromo-9-fluorenone was obtained as a yellow solid with a yield of 99.2%.

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Abstract

The invention discloses a synthetic method of 2-Bromo-9-fluorenon and belongs to the technical field of synthesis of organic compounds. The synthetic method of the 2-Bromo-9-fluorenon includes the following steps that firstly, 9-fluorenone and a phase transfer catalyst are mixed with an ammonium bromide aqueous solution and then are heated to 40 DEG C to 95 DEG C, the mixed solution is added to potassium bromate for reaction in batches, and the mole ratio of the 9-fluorenone, the ammonium bromide and the potassium bromate is 1:2-4:1-1.25;secondly, the mixed solution is cooled to the indoor temperature after reaction is completed, bromine removal fluid is added, and then the 2-Bromo-9-fluorenon is obtained through filtering and washing. The synthetic method of the 2-Bromo-9-fluorenon is easy and safe to operate, good in reaction selectivity and high in yield.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of 2-bromo-9-fluorenone. Background technique [0002] Fluorene and its derivatives have the characteristics of a large conjugated system in the molecule, a rigid planar biphenyl structure, a wide energy gap, a high luminous efficiency, and easy modification of the structure, making them widely used in electroluminescent materials. , solar cell materials and other fields have a wide range of applications. [0003] 2-Bromo-9-fluorenone is an important intermediate for the preparation of fluorene series derivatives. Both CN101514161 and CN101148402 have proposed a method for synthesizing 2-bromo-9-fluorenone from 9-fluorenone and elemental bromine, but elemental bromine It is volatile and highly toxic, which is not conducive to the reaction operation, and it is prone to leakage and pollutes the environment. Contents of the invent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/697C07C45/63
Inventor 王永张立攀王法云郭青照任钊周莉张亚勋智军丽
Owner HENAN BUSINESS SCI RES INST
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