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Synthesis method of 3-methyl-4-nitrodibenzofuran

A synthetic method, nitro technology, applied in the direction of organic chemistry, etc., can solve the problems of unfavorable industrial production preparation, low reaction yield, high price, etc., and achieve the effect of avoiding expensive raw materials, simple synthetic method, and cheap raw materials

Active Publication Date: 2020-06-02
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In this method, the first step reaction needs to use expensive 2-nitro-3-fluorotoluene, and the second step reaction yield is low, only 52%, so the overall cost of the synthesis method is high and unfavorable for industrial production preparation

Method used

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  • Synthesis method of 3-methyl-4-nitrodibenzofuran
  • Synthesis method of 3-methyl-4-nitrodibenzofuran
  • Synthesis method of 3-methyl-4-nitrodibenzofuran

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preparation example Construction

[0025] The invention provides a kind of synthetic method of 3-methyl-4-nitro-dibenzofuran, comprising the following steps:

[0026] S1, o-chlorophenol reacts with base I to form a salt, and then reacts with 2-nitro-3-chlorotoluene to obtain mixture I through nucleophilic substitution reaction, and intermediate 1 is obtained from mixture I after post-treatment;

[0027] S2. Dissolve intermediate 1 and 1,3-bis(2,6-diisopropylphenyl) imidazolium chloride in an aprotic polar solvent, and carry out intramolecular close under the action of Pd catalyst and base II Ring reaction to obtain mixture II, which is post-treated to obtain 3-methyl 4-nitro-dibenzofuran;

[0028] Its synthetic route is as follows:

[0029]

Embodiment 1

[0032] A kind of synthetic method of 3-methyl-4-nitro-dibenzofuran, specifically comprises the following steps:

[0033] first step:

[0034]

[0035] Under the protection of an inert gas, add 1896g of 50% KOH aqueous solution to the reaction bottle, dropwise add 1890g of o-chlorophenol in an ice-water bath, add 1700g of 2-nitro-3-chlorotoluene after the dropwise addition and stir at room temperature for 1 hour, and raise the temperature to 150°C React 30h and stop heating. Cool down to 60°C, add 22000ml of methylcyclohexane and stir for 0.5h, filter, and wash the filtrate with hot water until neutral. The organic phase was concentrated at 103°C under normal pressure, the residue was distilled, and the main fraction was recrystallized from methylcyclohexane to obtain 1627.6g of intermediate 1 with a yield of 62.3% and GC>99.3%.

[0036] Step two:

[0037]

[0038] Under the protection of an inert gas, add dimethylacetamide (DMAc) 1000ml to the reaction flask, intermed...

Embodiment 2

[0040] A kind of synthetic method of 3-methyl-4-nitro-dibenzofuran, specifically comprises the following steps:

[0041] first step:

[0042]

[0043] Under the protection of an inert gas, add 810 g of 50% KOH solution to the reaction flask, add 770 g of o-chlorophenol (1.3) dropwise under ice bath, add 800 g of 2-nitro-3-chlorotoluene after stirring at room temperature for 1 h after the addition, and heat up React at 160°C for 24h and stop heating. Cool down to 50°C, add 5000ml of methylcyclohexane and stir for 0.5h, filter, and wash the filtrate with hot water until neutral. The organic phase was concentrated at 82°C under normal pressure, the residue was distilled, and the main fraction was recrystallized with methylcyclohexane to obtain 736.8 g of intermediate 1 with a yield of 59.93% and GC>99.0%.

[0044] Step two:

[0045]

[0046] Under the protection of an inert gas, add 600ml of DMA, 300g of intermediate I, 315g of potassium carbonate, 5.1g of palladium acet...

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Abstract

The invention discloses a synthesis method of 3-methyl-4-nitrodibenzofuran, and belongs to the technical field of organic synthesis. The synthesis method comprises the following steps: S1, reacting o-chlorophenol with an alkali I to form a salt, then performing a nucleophilic substitution reaction on the salt and 2-nitro-3-chlorotoluene to obtain a mixture I, and performing post-treatment on the mixture I to obtain an intermediate 1; and S2, dissolving the intermediate 1 and 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride in an aprotic polar solvent, performing an intramolecular cyclizationreaction under the action of a Pd catalyst and an alkali II to obtain a mixture II, and performing post-treatment on the mixture II to obtain 3-methyl-4-nitrodibenzofuran. The synthesis method has the advantages of simplicity, cheap raw materials, easiness in purification, and avoiding of the problems of expensive raw materials and low yield in the traditional method.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3-methyl-4-nitro-dibenzofuran. Background technique [0002] The nitro group in 3-methyl-4-nitro-dibenzofuran is easily reduced to an amine group, and then the conjugated ring of the molecule is expanded by reactions such as Ullman and Buchwald-Hartwig. As a raw material, it is widely used In the synthesis reaction of photoelectric materials, it is widely used in the field of organic light-emitting diodes (CN110267943). [0003] The synthetic method of the currently reported 3-methyl-4-nitro-dibenzofuran is as follows: [0004] [0005] In this method, the first step reaction needs to use expensive 2-nitro-3-fluorotoluene, and the second step reaction yield is low, only 52%, so the overall cost of the synthesis method is high and unfavorable for industrial production preparation. Contents of the invention [0006] In order to so...

Claims

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Application Information

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IPC IPC(8): C07D307/91
CPCC07D307/91
Inventor 王轩贾小伟毛涛王小伟
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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