Synthetic method for 1,3,5-triarylbenzene compound

A synthesis method and technology of triarylbenzene, which are applied in the field of synthesis of 1,3,5-triarylbenzene compounds, can solve the problems of difficult preparation of substrates, harsh reaction conditions, narrow substrate range, etc. Easy post-processing and high applicability

Active Publication Date: 2015-11-11
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, 1,3,5-triarylbenzene compounds are mainly prepared by the condensation reaction of acetophenone and substituted acetophenone under the catalysis of various acids, but there are still many problems, such as: the su

Method used

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  • Synthetic method for 1,3,5-triarylbenzene compound
  • Synthetic method for 1,3,5-triarylbenzene compound
  • Synthetic method for 1,3,5-triarylbenzene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of 1,3,5-triphenylbenzene

[0023] Add 0.25mmol of chalcone, 1.5mmol of sodium tert-butoxide, and 2.0mL of dimethyl sulfoxide into a 10mL reaction tube, place in an oil bath at 60°C, and expose to air for 5h. Stop the reaction and cool to room temperature. The reaction solution was diluted with ethyl acetate, extracted three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, and separate by column chromatography to obtain 28.2 mg of the target product, with a yield of 77%. The NMR characterization of this compound is as follows: 1 HNMR (400MHz, CDCl 3 )δ7.78(s,3H),7.73–7.67(m,6H),7.51–7.44(m,6H),7.42–7.35(m,3H); 13 CNMR (100MHz, CDCl 3 )δ142.35, 141.16, 128.84, 127.54, 127.36, 125.17.

Embodiment 2

[0025] Preparation of 1-(4-methoxyphenyl)-3,5-diphenylbenzene

[0026] Add 0.25mmol of 4'-methoxychalcone, 1.5mmol of sodium tert-butoxide, and 2.0mL of dimethyl sulfoxide into a 10mL reaction tube, place it in an oil bath at 60°C, and expose it to the air for 5h . Stop the reaction and cool to room temperature. The reaction solution was diluted with ethyl acetate, extracted three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dried, filtered, and separated by column chromatography to obtain 25.6 mg of the target product with a yield of 63%. The NMR characterization of this compound is as follows: 1 HNMR (400MHz, CDCl 3 )δ7.78(s,1H),7.76–7.71(m,1H),7.68(d,J=8.7Hz,1H),7.51(t,J=7.6Hz,1H),7.42(t,J=7.3 Hz,1H),7.05(d,J=8.7Hz,1H),3.91(s,1H); 13 CNMR (100MHz, CDCl 3 )δ159.40, 142.34, 141.94, 141.28, 133.68, 128.84, 128.39, 127.51, 127.38, 124.79, 124.66, 114.32, 55.40.

Embodiment 3

[0028] Preparation of 1-(4-tert-butylphenyl)-3,5-diphenylbenzene

[0029] Add 0.25mmol of 4'-tert-butylchalcone, 1.5mmol of sodium tert-butoxide, and 2.0mL of dimethyl sulfoxide into a 10mL reaction tube, place it in an oil bath at 60°C, and expose it to the air for 5h . Stop the reaction and cool to room temperature. The reaction solution was diluted with ethyl acetate, extracted three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dried, filtered, and separated by column chromatography to obtain 27.4 mg of the target product with a yield of 49%. The NMR characterization of this compound is as follows: 1 HNMR (400MHz, CDCl 3 )δ7.81(dd, J=6.4,1.3Hz,3H),7.78–7.71(m,4H),7.68(d,J=8.3Hz,2H),7.53(dd,J=15.5,8.1Hz,6H ),7.42(t,J=7.3Hz,2H),1.42(s,9H); 13 CNMR (100MHz, CDCl 3 )δ150.63, 142.28, 142.23, 141.26, 138.27, 128.86, 127.52, 127.37, 127.03, 125.83, 125.10, 124.96, 34.61, 31.41.

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Abstract

The invention discloses a synthetic method for a 1,3,5-triarylbenzene compound. The method comprises the following steps: dissolving a chalcone derivative and inorganic alkali in dimethyl sulfoxide, carrying out reaction at 40 to 80 DEG C in the air for 3 to 8 hours, and carrying out separation and purification so as to obtain the 1,3,5-triarylbenzene compound, wherein a molar ratio of the chalcone derivative to the inorganic alkali is 1: 1-6; every mole of the chalcone derivative requires 4 to 8 mL of dimethyl sulfoxide; and the chalcone derivative has a general structural formula described in the specification, wherein Ar1 and Ar2 are aryl groups. The synthetic method for the 1,3,5-triarylbenzene compound provided by the invention has the following advantages of easily-available raw materials, simple operation, mild reaction conditions, no need of any transition metal catalyst, strong reaction specificity, strong applicability to a basic-group-contained substrate, no generation of waste products like halogen or boric acid, and simple, convenient and green after-treatment.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 1,3,5-triarylbenzene compounds. Background technique [0002] 1,3,5-Triarylbenzene compounds are a class of aromatic compounds with a special structure of C3 symmetry. They have 3 symmetry axes and 3 symmetry planes and are highly symmetrical, so they can be used to construct dendrimers and various Core module for polyphenylene compounds. The nonlinear macromolecules of its triaryl benzene mother ring have highly delocalized Π electrons and excellent optical, electrical, and magnetic properties. It is a class of electroluminescent organic molecular materials with great potential and important organic synthesis intermediates. It can also be used as an important basic functional module of hyperbranched polymer light-emitting materials. [0003] As early as the beginning of the 20th century, 1,3,5-triarylbenzene compounds have been synth...

Claims

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Application Information

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IPC IPC(8): C07C15/14C07C1/207C07C43/205C07C41/30C07C25/18C07C17/263C07C15/24C07D213/127C07D213/16C07C321/28C07C319/20C07D333/08C07F17/02
Inventor 崔秀灵王富源
Owner HUAQIAO UNIVERSITY
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