Synthesis method of triphenylene compound

A synthesis method and a triphenylene technology are applied in the field of synthesis of triphenylene compounds, and can solve the problems of harsh reaction conditions, unrecoverable catalysts, etc., and achieve the effects of mild reaction conditions and easy realization.

Active Publication Date: 2020-09-18
ANHUI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, such reactions often require the addition of transition metals or noble metals as catalysts.
The reality of harsh reaction conditions and non-recyclable catalysts is a huge challenge for environmental protection and control of reaction costs

Method used

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  • Synthesis method of triphenylene compound
  • Synthesis method of triphenylene compound
  • Synthesis method of triphenylene compound

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Experimental program
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Embodiment 1

[0027] A kind of synthetic method of triphenylene compound, described synthetic method comprises the following steps:

[0028] Raw material preparation:

[0029] 9-Fluorenone oxime, purity>97%, TCI (Shanghai) Chemical Industry Development Co., Ltd.;

[0030] 2-(Trimethylsilyl)phenyltrifluoromethanesulfonate, purity>95%, TCI (Shanghai) Chemical Industry Development Co., Ltd.

[0031] Specific synthesis process:

[0032] Under the condition of 66°C, 1.0mmol of 9-fluorenone oxime and 1.2mmol of 2-(trimethylsilyl)phenyltrifluoromethanesulfonate and 2.0mmol of cesium fluoride as base and 2mmol of 18-crown -6-ether was used as a phase transfer catalyst and reacted in 2 mL of anhydrous toluene solvent for 28 hours to obtain the crude product of the triphenylene compound; the crude product of the prepared triphenylene compound was washed with water, extracted with ethyl acetate, and spin-dried under reduced pressure, The volume ratio of ethyl acetate:petroleum ether=1:60 was separa...

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Abstract

The invention provides a synthesis method of a triphenylene compound. By taking 2-(trimethylsilyl)phenyl trifluoromethane sulfonate as a benzyne precursor, cesium fluoride as an alkali and 18-crown-6-ether as a phase transfer catalyst, a reaction of the precursor with 9-fluorenone oxime under the condition of no additional metal catalyst is realized through a one-pot process reaction. The reactioncondition is mild and easy to realize, the reaction overcomes the defect that transition metal or noble metal catalysts are required to be added in the previous reaction, and a brand-new way is provided for developing the triphenylene compound.

Description

technical field [0001] The invention belongs to the field of organic compounds, in particular to a method for synthesizing triphenylene compounds. Background technique [0002] Triphenylene compound is an important basic skeleton monomer of polycyclic aromatic hydrocarbons, which can be used as the basic precursor of this compound to synthesize macromolecular compounds with multi-conjugated structures, and is widely used in the research of organic supramolecular materials. It is a raw material for organic synthesis, used in electrical insulation materials, ion exchange resins, dyes, etc. At the same time, it is also used to make functional organic materials, such as: discotic liquid crystals and organic light-emitting diodes. [0003] In the past, triphenylene compound synthesis methods (Scheme1) have been reported one after another, mainly as follows: [0004] [0005] However, such reactions often require the addition of transition metals or noble metals as catalysts....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/32C07C15/38
CPCC07C1/321C07C2603/42C07C15/38
Inventor 祝文静陈婕妤胡益民
Owner ANHUI NORMAL UNIV
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