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Preparation method of dibenzothiophene derivative

A technology of dibenzothiophene and derivatives, which is applied in the field of preparation of dibenzothiophene derivatives, and achieves the effects of simple preparation method, high yield and low reaction cost

Inactive Publication Date: 2014-01-29
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Lewis-acid-promoted direct preparation of dibenzothiophene from methylthio-containing triazenes has not been reported

Method used

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  • Preparation method of dibenzothiophene derivative
  • Preparation method of dibenzothiophene derivative
  • Preparation method of dibenzothiophene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] In a 100mL sealed tube, add 746 mg of 2-halogenated aryl triazene (CAS: 858318-04-4, see the literature for the synthesis method: Organic Letters, 7(13), 2543-2546, 2005), 2-methylsulfide 369 mg of phenylboronic acid, 47 mg of palladium tetrakistriphenylphosphine, and 1.304 g of cesium carbonate, and then 4 mL of 1,4-dioxane and 1 mL of water were added with a syringe. The reaction solution was stirred overnight at 100°C. After the reaction was completed, cool to room temperature, extract with a separatory funnel, concentrate the organic phase and pass through a silica gel column (the volume ratio of petroleum ether to ethyl acetate is 10:1) for purification to obtain 576 mg of product (V-1), with a yield of 78%. , the reaction process is shown in the following formula:

[0032]

[0033] The product prepared in the present embodiment is carried out nuclear magnetic resonance analysis, and the results are as follows:

[0034] 1 H NMR (400MHz, CDCl 3 ): δ8.05 (dd, ...

Embodiment 2

[0037] In a 100mL sealed tube, add 652 mg of 2-halogenated aryltriazene (CAS: 858318-12-4, see the literature for the synthesis method: Organic Letters, 7(13), 2543-2546, 2005), 2-methylsulfide 369 mg of phenylboronic acid, 47 mg of palladium tetrakistriphenylphosphine, and 1.304 g of cesium carbonate, and then 4 mL of 1,4-dioxane and 1 mL of water were added with a syringe. The reaction solution was stirred overnight at 100°C. After the reaction was finished, cool to room temperature, extract with a separatory funnel, concentrate the organic phase and then pass through a silica gel column (the volume ratio of petroleum ether to ethyl acetate is 10:1) for purification to obtain 587 mg of product (V-2), with a yield of 91%. , the reaction process is shown in the following formula:

[0038]

[0039] The product prepared in the present embodiment is carried out nuclear magnetic resonance analysis, and the results are as follows:

[0040] 1H NMR (400MHz, CDCl 3 ):δ7.58-7.60...

Embodiment 3

[0043] In a 100mL sealed tube, add 506 mg of 2-halogenated aryltriazene (CAS: 188966-38-3, see the literature for the synthesis method: Organic Letters, 8(2), 257-260, 2006), 2-methylsulfide 369 mg of phenylboronic acid, 47 mg of palladium tetrakistriphenylphosphine, and 1.304 g of cesium carbonate, and then 4 mL of 1,4-dioxane and 1 mL of water were added with a syringe. The reaction solution was stirred overnight at 100°C. After the reaction was completed, cool to room temperature, extract with a separatory funnel, concentrate the organic phase and pass through a silica gel column (the volume ratio of petroleum ether to ethyl acetate is 10:1) for purification to obtain 476 mg of product (V-3), with a yield of 80%. , the reaction process is shown in the following formula:

[0044]

[0045] The product prepared in the present embodiment is carried out nuclear magnetic resonance analysis, and the results are as follows:

[0046] 1 H NMR (400MHz, CDCl 3 ):δ7.55(d,J=8.0Hz,...

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Abstract

The invention discloses a method for preparing dibenzothiophene derivatives. The method comprises the following steps of: synthesizing dibenzothiophene derivatives with chemical formulas of (I), (III) or (IV) from methylmercapto-containing triazene compounds in an organic solvent under catalysis of lewis acid, wherein R1 is ethoxycarbonyl, cyano, hydrogen or acetyl; R2 is chlorine or methyl; R3 is chlorine; R4 is halogen, methyl or methoxyl; and R5 is styryl. The preparation method is simple and mild in reaction conditions and has wide application prospects in the industries of fine chemical engineering and pharmacy.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of dibenzothiophene derivatives. Background technique [0002] Dibenzothiophene derivatives are an important class of organic compounds, dibenzothiophene and alkyl derivatives (DBTs) especially 4-methyldibenzothiophene (4-MDBT), 4,6-dimethyl Dibenzothiophene (DMBT) is considered to be the most difficult desulfurization sulfide in diesel fractions. Therefore, using DBT, 4-MDBT and 4,6-DMDBT as model compounds for deep desulfurization of oil products has become a research hotspot at home and abroad ( Catalysis today, 1997, 36, 393). In addition, dibenzothiophene is also widely used in liquid crystal optoelectronic semiconductor materials, such as literature (J.Meter.Chem.2007, 17, 1421) reported that dibenzothiophene derivatives as a new semiconductor in the Research in field effect transistors. [0003] One of the most important methods of generating dibenz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/76C07D295/30
CPCC07D295/30C07D333/76
Inventor 陈万芝尚晓博
Owner ZHEJIANG UNIV
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