3-substituted dibenzothiophene and synthesis method thereof

A technology of dibenzothiophene and a synthesis method, applied in the direction of organic chemistry and the like, can solve problems such as being unsuitable for mass production operations of the process, unable to obtain high-purity final products, a large amount of waste acid and waste water, etc., and achieves simplified post-processing methods, The effect of low pollution and low equipment requirements

Active Publication Date: 2022-01-28
西安欧得光电材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The purpose of the present invention is to overcome the above-mentioned deficiencies in the prior art: 1, high requirement to equipment, aftertreatment is complicated; 2, reaction process produces a large amount of waste acid and waste water, pollutes environment; 3, diazonium salt reaction, operation has certain danger 4. There are many impurities, and high-purity final products cannot be obtained; 5. It is not suitable for large-scale mass production operations.

Method used

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  • 3-substituted dibenzothiophene and synthesis method thereof
  • 3-substituted dibenzothiophene and synthesis method thereof
  • 3-substituted dibenzothiophene and synthesis method thereof

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preparation example Construction

[0038] The invention discloses a synthesis method of 3-substituted dibenzothiophene, comprising the following steps:

[0039] Step 1: Using o-iodoanisole and 4-substituted phenylboronic acid as starting materials, carry out coupling reaction to obtain intermediate a, the molar ratio of o-iodoanisole and 4-substituted phenylboronic acid is 1:1 ~1.4;

[0040]Step 2: Intermediate a, p-toluenesulfonic acid and hydrogen peroxide are oxidized to obtain intermediate b, and the molar ratio of intermediate a, p-toluenesulfonic acid and hydrogen peroxide is 1:0.5:1-1.2;

[0041] Step 3: Intermediate b and Eaton reagent undergo ring closure reaction to obtain 3-substituted dibenzothiophene, the molar ratio of intermediate b to Eaton reagent is 1:1-1.5; the 3-substituted dibenzothiophene The structural formula is Where R is Br, F, Cl, CF 3 , OH, benzene or NO 2 .

[0042] The Eaton reagent is 7.7wt% phosphorus pentoxide in methanesulfonic acid solution, this reagent can replace poly...

Embodiment 1

[0055]

[0056] in, is o-iodoanisole, For phenylboronic acid.

[0057] Step 1: Under nitrogen protection, add o-iodoanisole (2.50kg, 10mol), phenylboronic acid (1.46kg, 12mol), toluene 10L, ethanol 5L, water 5L, potassium carbonate (2.76kg, 20mol ), after adding, stir, heat up to 60-70°C, quickly add tetrakis(triphenylphosphine) palladium (115g, 0.1mol), continue to heat up to 75-80°C for reflux reaction for 10h, after the reaction is completed, cool down, and use toluene Extract the reaction system, wash the organic phase with water, dry the organic phase, filter and remove the desiccant, concentrate the organic phase, recrystallize the concentrate using methanol to HPLC > 98.5%, and dry to obtain intermediate a-1 with a yield of 90.2%.

[0058] Step 2: Add intermediate a-1 (1.80kg, 9mol) and p-toluenesulfonic acid (0.856g, 4.5mol) prepared in the previous step to the reaction flask, add 7.2L of dichloroethane to dissolve and clarify, and 30°C, add 30% H 2 o 2 (1.02...

Embodiment 2

[0062]

[0063] in, is o-iodoanisole, For p-bromophenylboronic acid.

[0064] Step 1: Under nitrogen protection, add o-iodoanisole (2.5kg, 10mol), p-bromophenylboronic acid (1.46kg, 12mol), toluene 10L, ethanol 5L, water 5L, potassium carbonate (2.76kg , 20mol), after adding, stir, heat up to 60-70°C, quickly add tetrakis(triphenylphosphine) palladium (115g, 1mol), continue to heat up to 75-80°C for reflux reaction for 10h, after the reaction is completed, cool down, use Extract the reaction system with toluene, wash the organic phase with water, dry the organic phase, filter and remove the desiccant, concentrate the organic phase, recrystallize the concentrate with methanol to HPLC > 97.8%, and dry to obtain intermediate a-2 with a yield of 65.5%.

[0065] Step 2: Add the intermediate a-2 (1.30kg, 6mol) and p-toluenesulfonic acid (0.570kg, 3mol) prepared in the previous step to the reaction flask, add 5.4L of dichloroethane to dissolve and clarify. °C, add 30% H 2 o ...

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Abstract

The invention discloses 3-substituted dibenzothiophene and a synthesis method thereof. The synthesis method comprises the steps of 1, taking o-iodoanethiol sulfide and 4-substituted phenylboronic acid as starting raw materials, and performing a coupling reaction to obtain an intermediate a, wherein the molar ratio of the o-iodoanethiol sulfide to the 4-substituted phenylboronic acid is 1: (1-1.4); 2, enabling the intermediate a, p-toluenesulfonic acid and hydrogen peroxide to be subjected to an oxidation reaction, and obtaining an intermediate b, wherein the molar ratio of the intermediate a to the p-toluenesulfonic acid to the hydrogen peroxide is 1: 0.5: (1-1.2); and 3, enabling the intermediate b and an Eaton reagent to be subjected to a ring closing reaction, and obtaining the 3-substituted dibenzothiophene, wherein the molar ratio of the intermediate b to the Eaton reagent is 1: (1-1.5).

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a 3-substituted dibenzothiophene and a synthesis method thereof. Background technique [0002] Organic compounds of dibenzothiophenes are widely used in organic light-emitting devices, and 3-substituted dibenzothiophenes are an important class of organic molecular skeletons. In the synthesis of the prior art, the 3-halogenated dibenzothiophenes process The cost is high, the reaction process produces a lot of waste water, the pollution is high, the risk is high, the requirements for equipment are high, and the post-treatment is difficult. The following describes the shortcomings of the existing process with reference to the existing synthetic route. [0003] The synthesis method of this type of compound mainly contains following several kinds at present: [0004] Conventional route 1 (refer to JP2018090561, WO2017196081A1, WO2002078693) [0005] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/76
CPCC07D333/76
Inventor 王荣任莺歌郭红梅李涛
Owner 西安欧得光电材料有限公司
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