Synthetic method of 2,7-dibromo-benzo[9,10]phenanthrene

A synthetic method, the technology of dibromobiphenyl, applied in 2 fields, can solve the problems of low yield, incapable of mass production environment, poor selectivity, etc., and achieve the effect of short process route

Active Publication Date: 2019-04-23
山东瑞辰新材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The invention provides a synthesis method of 2,7-dibromo-benzo[9,10]phenanthrene, which is used to synthesize triphe

Method used

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  • Synthetic method of 2,7-dibromo-benzo[9,10]phenanthrene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 31.2g of 4,4'-dibromobiphenyl was dissolved in 312ml of dichloromethane, the temperature of the control system was between 10-15°C, and 11.0g of concentrated nitric acid (65%) and 10.5g of concentrated sulfuric acid (98%) were slowly added dropwise. ) mixed solution, after the dropwise addition, keep warm at 10-15°C and react for 2h, the reaction solution is washed with water, dried, and concentrated to obtain a crude product, which is recrystallized three times with ethanol according to the ratio of crude product: ethanol = 1g: 5ml, and vacuum-dried Dry to obtain 29.8g of 2-nitro-4,4'-dibromobiphenyl, yield: 83.5%, GC content 99.6%.

[0033] Add 29.8g of 2-nitro-4,4'-dibromobiphenyl into the mixed system of 150ml of ethanol and 30ml of water, add 26.8g of ammonium chloride, 28.0g of iron powder, start stirring, heat, reflux for 2h, and react The liquid was extracted with dichloromethane, washed with water, dried, and concentrated under reduced pressure to obtain 26.5 g...

Embodiment 2

[0038] 31.2g of 4,4'-dibromobiphenyl was dissolved in 312ml of dichloromethane, the temperature of the control system was between 10-15°C, and 11.0g of concentrated nitric acid (65%) and 10.5g of concentrated sulfuric acid (98%) were slowly added dropwise. ) mixed solution, after the dropwise addition, keep warm at 10-15°C for 2 hours, the reaction solution is washed with water, dried, concentrated, and recrystallized from ethanol to obtain 30.3g of 2-nitro-4,4'-dibromobiphenyl.

[0039] Add 30.3g of 2-nitro-4,4'-dibromobiphenyl into the mixed system of 151ml of ethanol and 30ml of water, add 27.2g of ammonium chloride, 28.5g of iron powder, start stirring, heat, reflux for 2h, and react The liquid was extracted with dichloromethane, washed with water, dried and concentrated to obtain 27.2 g of 2-amino-4,4'-dibromobiphenyl.

[0040] Dissolve 27.2g of 2-amino-4,4'-dibromobiphenyl in 272ml of benzene, add 17.6g of trichloroacetic acid and 0.4g of cuprous chloride in sequence, st...

Embodiment 3

[0044] 31.2g of 4,4'-dibromobiphenyl was dissolved in 312ml of dichloromethane, the temperature of the control system was between 10-15°C, and 11.0g of concentrated nitric acid (65%) and 10.5g of concentrated sulfuric acid (98%) were slowly added dropwise. ) mixed solution, after the dropwise addition, keep warm at 10-15°C for 2 hours, the reaction solution is washed with water, dried, concentrated, and recrystallized from ethanol to obtain 30.1g of 2-nitro-4,4'-dibromobiphenyl.

[0045] Add 30.1g of 2-nitro-4,4'-dibromobiphenyl into the mixed system of 150ml of ethanol and 30ml of water, add 27.0g of ammonium chloride, 28.3g of iron powder, start stirring, heat, reflux for 2h, and react The liquid was extracted with dichloromethane, washed with water, dried and concentrated to obtain 27.1 g of 2-amino-4,4'-dibromobiphenyl.

[0046] Dissolve 27.1g of 2-amino-4,4'-dibromobiphenyl in 271ml of benzene, add 17.5g of trichloroacetic acid and 0.4g of cuprous chloride in sequence, st...

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and relates to a synthetic method of triphenylene, in particular to a synthetic method of 2,7-dibromo-benzo[9,10]phenanthrene. The synthetic method includes dissolving 4,4'-dibromobiphenyl in dichloromethane; adopting a mixed solution of nitric acid and sulfuric acid for nitration reaction, and carrying out washing, concentrating and recrystallizing to obtain 2-nitro-4,4'-dibromobiphenyl, wherein the yield is 82%; reducing a nitro group into an amino group by a Fe/NH4Cl system, and subjecting the obtained product and benzene to diazo coupling reaction to obtain 4,4'-dibromo-1,1',2',1-terphenyl; performing oxidative coupling by a Pd/trifluoromethanesulfonic acid system to obtain the 2,7-dibromo-benzo[9,10]phenanthrene, wherein the yield is 62.5%, and the HPCL purity is 99.5%. The synthetic method avoids the problems of complex synthesis, low yield and environmental pollution in conventional methods.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a synthesis method of triphenylene, in particular to a synthesis method of 2,7-dibromo-benzo[9,10]phenanthrene. Background technique [0002] 2,7-Dibromo-benzo[9,10]phenanthrene is a derivative of triphenylene. Triphenylene is a typical discotic liquid crystal composed of three benzene rings. The discotic liquid crystal material can form a unique columnar Phase structure, in the columnar phase, the molecular arrangement of the system has a one-dimensional order, and at the same time, due to the π-electron conjugation of the discotic mesogen itself, a quasi-one-dimensional conjugation is formed along the direction of the molecular column axis. Electron cloud distribution, in addition, it also has the unique properties of discotic liquid crystals such as electroluminescent effect, ferroelectric properties and surface self-assembly, these properties make discotic li...

Claims

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Application Information

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IPC IPC(8): C07C17/35C07C25/22C07C17/263C07C25/18
CPCC07C17/263C07C17/35C07C201/08C07C209/325C07C25/22C07C205/12C07C211/52C07C25/18
Inventor 陈丽娟张芳杨建飞朱振国
Owner 山东瑞辰新材料有限公司
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