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Production method for 4-bromo fluorenone

A production method, bromofluorenone technology, applied in the field of organic chemical synthesis, can solve problems such as high production cost, influence on market promotion, difficult industrial production, etc., and achieve the effect of reducing production cost

Active Publication Date: 2016-01-13
濮阳惠成新材料产业技术研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few reports on its production method. It mainly uses o-cyanophenylboronic acid as the starting material and is synthesized by coupling and ring closure. The production cost is high and it is difficult to industrialize production, which affects its market promotion, especially in the field of luminescent materials.

Method used

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  • Production method for 4-bromo fluorenone
  • Production method for 4-bromo fluorenone

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0020] Add 12mL of benzonitrile, 23.58g (0.1mol) of o-dibromobenzene, 22.8g (0.15mol) of cesium fluoride to a 250mL reaction flask, and add 0.67g (3mmol) of palladium acetate and thiophene-2- 0.57g (3mmol) of cuprous formate and 1.4g (3mmol) of 1,1'-bis(di-tert-butylphosphino)ferrocene, reacted at 120°C for 36h, filtered, and the filtrate was distilled to remove benzonitrile to obtain 2-bromo - Crude 2'-carbonitrile biphenyl. In a 100mL reaction flask, add 2-bromo-2'-formonitrile biphenyl, 25mL glacial acetic acid, 25mL concentrated sulfuric acid, heat to reflux for 12h, cool to room temperature, filter, wash with 50mL of water, wash with 50mL of methanol, and re- Crystallization gave 19.6 g of yellow solid 4-bromofluorenone, with a yield of 76%.

[0021] Melting point: 127.2-128.9°C.

[0022] 1 HNMR (400Hz, DMSO-d 6 ), δ / ppm: 8.348-8.33(d,1H; J=7.2Hz), 7.697-7.679(d,1H; J=7.2Hz), 7.625-7.558(m,3H), 7.355-7.335(t,1H ;J=8.0Hz), 7.157-7.138(t,1H;J=7.6Hz);

[0023] 13 CNMR...

example 2

[0025] Add 30mL of benzonitrile, 47.1g (0.2mol) of o-dibromobenzene, 45.6g (0.3mol) of cesium fluoride to a 250mL reaction flask in sequence, and add 4.63g (4mmol) of tetrakis(triphenylphosphine)palladium after argon replacement. ), 0.77g (4mmol) of cuprous thiophene-2-carboxylate and 1.94g (4mmol) of 1,1'-bis(di-tert-butylphosphino)ferrocene, reacted at 130°C for 30h, filtered, and the filtrate was distilled to remove benzyl Nitrile to obtain crude 2-bromo-2'-formonitrile biphenyl. Add crude 2-bromo-2'-carbonitrile biphenyl, 50 mL of glacial acetic acid, and 50 mL of concentrated sulfuric acid into a 250 mL reaction flask in sequence. After heating to reflux for 12 hours, cool to room temperature, filter to obtain a dark yellow solid, wash with 80 mL of water, wash with 100 mL of methanol, and recrystallize from 140 mL of cumene to obtain 37.6 g of a yellow solid, namely 4-bromofluorenone, with a yield of 73%.

example 3

[0027] Add 50mL of benzonitrile, 70.7g (0.3mol) of o-dibromobenzene, and 68.4g (0.45mol) of cesium fluoride to a 500mL reaction flask in sequence, and add 0.86g of catalyst bis(dibenzylideneacetone) palladium after argon replacement (15mmol), 2.86g (15mmol) of cuprous thiophene-2-carboxylate and 7.0g (15mmol) of 1,1'-bis(di-tert-butylphosphino)ferrocene, reacted at 150°C for 24h, filtered, and the filtrate was distilled off Benzonitrile yields crude 2-bromo-2'-carbonitrile biphenyl. Add crude 2-bromo-2'-carbonitrile biphenyl, 80 mL of glacial acetic acid, and 80 mL of concentrated sulfuric acid into a 500 mL reaction flask in sequence. After heating to reflux for 12 hours, cool to room temperature, and filter to obtain a dark yellow solid, which was washed with 100 mL of water and 100 mL of methanol, and recrystallized from 200 mL of cumene to obtain 61.9 g of 4-bromofluorenone as a yellow solid, with a yield of 80%.

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Abstract

The invention discloses a production method for 4-bromo fluorenone, belonging to the field of organic chemical synthesis. The production method is realized by comprising the following steps: reacting cyanobenzene as a raw material with o-dibromobenzene under the protection of argon gas and the actions of a palladium catalyst, a copper catalyst and an organic phosphine ligand so as to obtain 2-bromo-2'-carbonitrile biphenyl, and carrying out hydrolyzation and closed-loop synthesizing so as to obtain the 4-bromo fluorenone. The production method for the 4-bromo fluorenone is simple to operate in reaction process, has low production cost and is suitable for industrial production. The 4-bromo fluorenone can be applied in the fields of organic optoelectronic materials, medicines, pesticides, etc.

Description

technical field [0001] The invention relates to a production method of fluorene compounds, in particular to a production method of 4-bromofluorenone, which belongs to the field of organic chemical synthesis. Background technique [0002] Fluorene derivatives are a class of luminescent materials with promising applications. Fluorene has high photothermal stability, the solid-state fluorene fluorescence quantum efficiency is as high as 60%-80%, and the band gap energy is greater than 2.90eV. Fluorene has a certain modifiability in structure, but the rigid planar biphenyl unit of fluorene makes it easy for the material to form excimer associations when emitting light to produce long-wave emission, which affects the saturation color purity and luminous color of the emitted light from the device. stability. In order to improve the comprehensive luminescent performance of fluorene materials, introducing large groups or side chains with steric hindrance effect on the structure of...

Claims

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Application Information

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IPC IPC(8): C07C49/697C07C45/00
CPCC07C45/00C07C253/30C07C49/697C07C255/50
Inventor 杨振强陈鹏丽杨瑞娜陈辉屈凤波孙敏青周铎
Owner 濮阳惠成新材料产业技术研究院有限公司
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