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A method for synthesizing 1-chloro-2-bromobenzo[9,10]phenanthrene

A technology of bromobenzene and bromochlorobenzene is applied in the synthesis field of 1-chloro-2-bromobenzo[9,10]phenanthrene, and can solve problems such as time-consuming, environmental pollution, complex synthesis process and the like

Active Publication Date: 2016-03-09
JINING XINRUIDA INFORMATION TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In order to solve the problems of time-consuming, complex synthesis process and easy environmental pollution in the prior art, the invention provides a method for synthesizing 1-chloro-2-bromobenzo[9,10]phenanthrene, using the The method synthesizes triphenylene derivatives, which avoids the problems of complex synthesis, inability to produce in large quantities, and side reactions such as environmental pollution in traditional methods

Method used

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  • A method for synthesizing 1-chloro-2-bromobenzo[9,10]phenanthrene

Examples

Experimental program
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Effect test

example 1

[0015] Put 17.63g bromochlorobenzene and 23.73gde succinic anhydride into the reaction flask and stir well, then add 20.52mL, 1.62mmol HB(OH) 2 Heat to 40°C, stir evenly, and then place to room temperature; under the protection of nitrogen, add 15.62g of 2-bromobenzaldehyde and 90mL of ethanol to a dry 500mL four-necked reaction flask, and then place it at room temperature. The solution was added to a four-necked reaction flask, and after stirring evenly, 86.0g of 20% sodium carbonate aqueous solution was added, and then 1.0g of tetrakis(triphenylphosphine)palladium was quickly added, heated from room temperature to 70°C and refluxed, and heated for 2 hours; Add 7.26g of 2-bromobenzaldehyde to the reaction flask, stir evenly with 45mL of ethanol, add 86.0g of 20% sodium carbonate aqueous solution, and then quickly add 0.5g of tetrakis(triphenylphosphine)palladium, and heat up from room temperature to 70℃ and reflux The reaction was kept stirring at this temperature for 6 hours t...

example 2

[0017] Put 17.63g bromochlorobenzene and 23.73gde succinic anhydride into the reaction flask and stir well, then add 20.52mL, 1.62mmol HB(OH) 2 Heat to 45°C, stir evenly, and place to room temperature; under the protection of nitrogen, add 15.62g of 2-bromobenzaldehyde and 90mL of ethanol to a dry 500mL four-necked reaction flask, and then place it at room temperature. Add the solution to a four-necked reaction flask, stir well and add 86.0g of 20% sodium carbonate aqueous solution, then quickly add 1.0g of tetrakis(triphenylphosphine) palladium, heat up from room temperature to 75°C and reflux for 2 hours; Add 7.26g of 2-bromobenzaldehyde to the reaction flask, stir evenly with 45mL of ethanol, add 86.0g of 20% sodium carbonate aqueous solution, and then quickly add 0.5g of tetrakis(triphenylphosphine)palladium, and heat from room temperature to 75°C for reflux The reaction was kept stirring at this temperature for 6 hours to sample for HPLC control. The reaction of 2-bromoben...

example 3

[0019] Put 17.63g bromochlorobenzene and 23.73gde succinic anhydride into the reaction flask and stir well, then add 20.52mL, 1.62mmol HB(OH) 2 Heat to 550°C, stir evenly, and place to room temperature; under the protection of nitrogen, add 15.62g of 2-bromobenzaldehyde and 90mL of ethanol to a dry 500mL four-necked reaction flask, and then place it at room temperature. Add the solution to a four-necked reaction flask, stir well, add 86.0g of 20% sodium carbonate aqueous solution, and then quickly add 1.0g of tetrakis (triphenylphosphine) palladium, heat up from room temperature to 80°C and reflux for 2.5 hours; Add 7.26g of 2-bromobenzaldehyde to the reaction flask, stir evenly with 45mL of ethanol, add 86.0g of 20% sodium carbonate aqueous solution, and then quickly add 0.5g of tetrakis(triphenylphosphine)palladium, and heat from room temperature to 80°C for reflux The reaction was kept stirring at this temperature for 6 hours to sample for HPLC control. The reaction of 2-bro...

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Abstract

The invention discloses a method for synthesizing 1-chloro-2-bromobenzo[9,10]phenanthrene, which comprises the following steps: putting chlorobenzene and butanedioic anhydride into a reaction bulb, sufficiently stirring, adding HB(OH)2, heating to 40-50 DEG C, stirring uniformly, and standing to room temperature; adding 7.26g of 2-bromobenzaldehyde and 45mL of ethanol into the reaction bulb twice, stirring uniformly, adding 86.0g of 20% sodium carbonate water solution, quickly adding tetra(triphenylphosphine) palladium, heating from room temperature to 70-80 DEG C (under reflux), keeping stirring at such temperature to react for 6 hours, sampling, and carrying out HPLC (high performance liquid chromatography) central control; after the 2-bromobenzaldehyde is reacted completely, cooling the reaction solution to 25-30 DEG C, and dropwisely adding methanesulfonic acid at room temperature; and after the reaction finishes, adding potassium carbonate into the reaction bulb, carrying out phase splitting, filtering and precipitating the solid powder, wherein the yield is 60.12%, and the HPLC is 99.12%. The method avoids the problems of complex synthesis, incapability of mass production, environmental pollution, side reactions and the like in the traditional method.

Description

Technical field [0001] The invention belongs to the field of organic chemical synthesis, and relates to a method for synthesizing triphenylene, in particular to a method for synthesizing 1-chloro-2-bromobenzo[9,10]phenanthrene. Background technique [0002] 1-Chloro-2-bromobenzo[9,10]phenanthrene is a derivative of Sanyaben. Triphenylene is a typical columnar discotic liquid crystal composed of three benzene rings. It was first reported by Buess and Lawsons in 1960. A review on the synthesis of triphenylene compounds is presented, and it is determined that they have special liquid crystal properties and photoelectric functions. Its derivatives are chemically and thermally stable and can exhibit different liquid crystal phases. It has an 18-π-electron plane delocalization system. Because the triphenylene derivatives have many different types of liquid crystal phases and high-speed charge transport Mobility, so triphenylene derivatives have received widespread attention and began ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C25/22C07C17/361
Inventor 陈兴权
Owner JINING XINRUIDA INFORMATION TECH CO LTD
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