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

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

Active Publication Date: 2015-02-04
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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  • Method for synthesizing 1-chloro-2-bromobenzo[9,10]phenanthrene

Examples

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example 1

[0015] Put 17.63g of bromochlorobenzene and 23.73gde succinic anhydride into the reaction flask and stir thoroughly, then add 20.52mL, 1.62mmol of HB(OH) 2 Heat to 40°C, stir evenly, and place at 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 in sequence, and place the Add the solution into a four-necked reaction flask, stir evenly, add 86.0 g of 20% sodium carbonate aqueous solution, then quickly add 1.0 g of tetrakis(triphenylphosphine) palladium, raise the temperature from room temperature to 70° C. (reflux), and heat for 2 hours; Add 7.26g of 2-bromobenzaldehyde in the reaction flask again, add 86.0g20% sodium carbonate aqueous solution after the ethanol of 45mL is stirred evenly, then add 0.5g tetrakis (triphenylphosphine) palladium rapidly, be warming up to 70 from room temperature °C (reflux) and kept stirring at this temperature for 6 hours to take samples for HPLC cont...

example 2

[0017] Put 17.63g of bromochlorobenzene and 23.73gde succinic anhydride into the reaction flask and stir thoroughly, then add 20.52mL, 1.62mmol of HB(OH) 2 Heat to 45°C, stir evenly, and place it at 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 in sequence, and place the Add the solution into a four-necked reaction flask, stir evenly, add 86.0 g of 20% sodium carbonate aqueous solution, then quickly add 1.0 g of tetrakis(triphenylphosphine)palladium, raise the temperature from room temperature to 75° C. (reflux), and heat for 2 hours; Add 7.26g of 2-bromobenzaldehyde to the reaction flask again, add 86.0g20% sodium carbonate aqueous solution after stirring evenly after 45mL of ethanol, then quickly add 0.5g tetrakis (triphenylphosphine) palladium, heat up from room temperature to 75 °C (reflux) and kept stirring at this temperature for 6 hours to take samples for HPLC control....

example 3

[0019] Put 17.63g of bromochlorobenzene and 23.73gde succinic anhydride into the reaction flask and stir thoroughly, then add 20.52mL, 1.62mmol of HB(OH) 2 Heat to 550°C, stir evenly, and place it at 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 in sequence, and place the Add the solution into a four-necked reaction flask, stir evenly, add 86.0 g of 20% sodium carbonate aqueous solution, then quickly add 1.0 g of tetrakis(triphenylphosphine) palladium, raise the temperature from room temperature to 80° C. (reflux), and heat for 2.5 hours; Add 7.26g of 2-bromobenzaldehyde in the reaction flask again, add 86.0g20% sodium carbonate aqueous solution after the ethanol of 45mL is stirred evenly, add 0.5g tetrakis (triphenylphosphine) palladium fast then, be warming up to 80 from room temperature °C (reflux) and kept stirring at this temperature for 6 hours to take samples for HPLC c...

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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 synthesis method of triphenylene, in particular to a synthesis method of 1-chloro-2-bromobenzo[9,10]phenanthrene. Background technique [0002] 1-Chloro-2-bromobenzo[9,10]phenanthrene is a derivative of triphenylene. Triphenylene is a typical columnar phase 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 was made, and it was confirmed that it has special liquid crystallinity and optoelectronic functions. Its derivatives are chemically and thermally stable and can exhibit different liquid crystal phases. It has a delocalized system of 18-π-electron plane. Since triphenylene derivatives have a variety of different types of liquid crystal phases and high-speed charge transport Mobility, so triphenylene derivatives have received widespread attention and have begun...

Claims

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Application Information

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