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Preparation method of substituted benzo [B] naphthyl benzene [2, 3-D] thiophene derivative and derivative

A thiophene derivative, 3-D technology, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of high pollution of raw materials, high toxicity of chemical additives, complicated post-processing, etc., and achieve simple post-processing. , low cost, cheap and dangerous effect

Pending Publication Date: 2022-06-07
陕西维世诺新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In view of this, the purpose of the present invention is to provide a kind of preparation method of substituted benzo [B] naphthalene benzo [2,3-D] thiophene derivatives, solve the existing technology in preparing a kind of substituted benzo [B] naphthalene The preparation method of benzo[2,3-D]thiophene derivatives has the problems of large pollution of raw materials and high price, high toxicity of chemical auxiliary agents, many reaction steps, complicated process, low yield and complicated post-treatment

Method used

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  • Preparation method of substituted benzo [B] naphthyl benzene [2, 3-D] thiophene derivative and derivative
  • Preparation method of substituted benzo [B] naphthyl benzene [2, 3-D] thiophene derivative and derivative
  • Preparation method of substituted benzo [B] naphthyl benzene [2, 3-D] thiophene derivative and derivative

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Effect test

Embodiment 1

[0044] Preparation of Benzo[B]naphtho[2,3-D]thiophene

[0045] Using 2-naphthyl methyl sulfide as a raw material to react at low temperature to obtain intermediate S1, the intermediate S1 and o-fluoroiodobenzene undergo a coupling reaction to obtain intermediate S2, and the intermediate S2 is carried out under the action of Lewis acid The demethylation reaction obtains S3, and the S3 undergoes a ring-closing reaction under the action of a base to obtain a product W1: benzo[B]naphthalene[2,3-D]thiophene, and its chemical reaction formula is:

[0046]

[0047] The method is specifically implemented through the following steps:

[0048] 2-Naphthyl methyl sulfide (50g, 0.29mol) was added to a 1000ML reactor containing 500ml of tetrahydrofuran, then triisopropyl borate (70.2g, 0.37mol) was added, and after nitrogen was replaced, the temperature was lowered to -70~- 90°C, add n-butyllithium (149.4ml, 0.37mol) dropwise, control the temperature at -70~-90°C to fully react for 3~6h, ...

Embodiment 2

[0055] Preparation of 3-Bromobenzo[B]naphthalene[2,3-D]thiophene

[0056] Using 2-naphthyl methyl sulfide as a raw material to react at low temperature to obtain an intermediate S1, the intermediate S1 and 4-bromo-2-fluoroiodobenzene undergo a coupling reaction to obtain an intermediate S4, and the intermediate S4 is in Lewis The demethylation reaction is carried out under the action of an acid to obtain S5, and the S5 is subjected to a ring-closure reaction under the action of a base to obtain a product W5: 3-bromobenzo[B]naphthalene[2,3-D]thiophene, which is The chemical reaction formula is:

[0057]

[0058] The method is specifically implemented through the following steps:

[0059] Add 2-naphthyl methyl sulfide (50g, 0.29mol) into a 1000ML reactor containing 500ml of tetrahydrofuran, then add trimethyl borate (38.9g, 0.37mol), and after replacing nitrogen, reduce the temperature to -70~-90 ℃, add n-butyllithium (149.4ml, 0.37mol) dropwise, control the temperature to ...

Embodiment 3

[0066] Preparation of 2-Chlorobenzo[B]naphthalene[2,3-D]thiophene

[0067] Using 2-naphthyl methyl sulfide as a raw material to react at low temperature to obtain intermediate S1, the intermediate S1 is coupled with 5-chloro-2-fluoroiodobenzene to obtain intermediate S6, and the intermediate S6 is in Lewis The demethylation reaction is carried out under the action of an acid to obtain S7, and the S7 is subjected to a ring-closure reaction under the action of a base to obtain the product W10: 2-chlorobenzo[B]naphthalene [2,3-D]thiophene, which is The chemical reaction formula is:

[0068]

[0069] The method is specifically implemented through the following steps:

[0070] 2-Naphthyl methyl sulfide (50g, 0.29mol) was added to a 1000ML reactor containing 500ml of tetrahydrofuran, then tributyl borate (85.9g, 0.37mol) was added, and after nitrogen was replaced, the temperature was lowered to -70~-90 ℃, add n-butyllithium (149.4ml, 0.37mol) dropwise, control the temperature t...

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Abstract

The invention discloses a preparation method of a substituted benzo [B] naphthobenzene [2, 3-D] thiophene derivative, which comprises the following steps: reacting 2-naphthyl dimethyl sulfide serving as a raw material at low temperature to obtain an intermediate S-1, carrying out coupling reaction on the intermediate S-1 and substituted o-iodobenzene to obtain an intermediate S-2, and carrying out demethylation reaction on the intermediate S-2 under the action of Lewis acid to obtain S-3, 5-disubstituted benzo [B] naphthobenzene [2, 3-D] thiophene derivative. The S-3 is subjected to a ring closing reaction under the action of alkali, and the product W0: substituted benzo [B] naphthyl benzene [2, 3-D] thiophene derivative is obtained. By adopting the preparation method of the substituted benzo [B] naphthobenzene [2, 3-D] thiophene derivative provided by the invention, the obtained product is high in purity, high in yield and low in cost, no waste solvent is generated in the whole preparation process, and meanwhile, less waste water is generated, so that a foundation is laid for realizing the aim of environmental protection.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation method and a derivative of a substituted benzo[B]naphthalene[2,3-D]thiophene derivative. Background technique [0002] Substituted benzo[B]naphthalene[2,3-D]thiophenes have various applications due to their special structure. Introducing different active groups at the 1, 2, 3, and 4 positions of its structure will have different applications and better performance in different fields. Due to the continuous research and The development and introduction of various substituents at the 1, 2, 3, and 4 positions of benzo[B]naphthalene[2,3-D]thiophene requires increasingly higher purity and yield, and with the development of OLED organic light-emitting materials The continuous breakthroughs and marketization of the products have created a greater demand for their intermediate materials. Therefore, in order to obtain substituted benzo[B]napht...

Claims

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Application Information

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IPC IPC(8): C07D333/50C09K11/06
CPCC07D333/50C09K11/06C09K2211/1092Y02E10/549
Inventor 吕钟毕永林
Owner 陕西维世诺新材料有限公司
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