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Method for continuously preparing isobenzofuran compounds by using micro-channel reaction device

A microchannel reaction and compound technology, applied in organic chemistry, electrodes, electrolysis processes, etc., can solve problems such as the need for expensive catalysts and long reaction process cycles, and achieve the effects of good industrial amplification potential, low cost, and easy preparation process.

Active Publication Date: 2020-08-21
NANJING TECH UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] Purpose of the invention: the technical problem to be solved by this invention is to provide a method for continuously preparing isobenzofuran compounds using a microchannel reaction device to overcome the long reaction process period and the need for The Problem with Expensive Catalysts

Method used

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  • Method for continuously preparing isobenzofuran compounds by using micro-channel reaction device
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  • Method for continuously preparing isobenzofuran compounds by using micro-channel reaction device

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Embodiment 1

[0045] The synthesis of embodiment 1 compound 3a:

[0046] 0.2 mmol (0.060 g) of compound 1a, 0.2 mmol (0.062 g) of diphenyldiselenide 2a and 0.4 mmol of lithium perchlorate (0.043 g) were dissolved in acetonitrile (8 mL) to obtain a homogeneous solution A, which was added to In the syringe pump a; the injection flow rate of the syringe pump a is 450 μL / min; the applied current is 15 mA; the microchannel reactor reaction volume V=225 μL, and the reaction time is 30 s; The yield of the product calculated by HPLC was 86%, and the product 3a was obtained after separation by column chromatography. 1 H NMR (400MHz, Chloroform-d) δ7.92 (d, J = 8.2Hz, 2H), 7.82 (d, J = 5.6Hz, 1H), 7.40 (q, J = 7.8, 5.7Hz, 2H), 7.36 –7.31(m,1H),7.28(d,J=7.2Hz,2H),7.22(d,J=8.1Hz,2H),7.20–7.15(m,1H),7.12(t,J=7.2Hz, 2H), 5.83–5.77(m, 1H), 3.31(dd, J=13.3, 4.6Hz, 1H), 3.13(dd, J=13.3, 6.6Hz, 1H), 2.34(s, 3H). 13C NMR (101MHz, Chloroform-d) δ166.04, 145.43, 142.46, 137.18, 133.17, 132.78, 128.79, 128.26...

Embodiment 2

[0047] The synthesis of embodiment 2 compound 3a:

[0048] 0.2 mmol (0.060 g) of compound 1a, 0.2 mmol (0.062 g) of diphenyldiselenide 2a and 0.4 mmol of tetrabutylammonium hexafluorophosphate (0.155 g) were dissolved in acetonitrile (8 mL) to obtain a homogeneous solution A , added to syringe pump a; the injection flow rate of syringe pump a is 450μL / min; the applied current is 15mA; the microchannel reactor reaction volume V=225μL, and the reaction time is 30s; In the reaction liquid, the yield of the product calculated by HPLC was 70%, and the product 3a was obtained after separation by column chromatography.

Embodiment 3

[0049] The synthesis of embodiment 3 compound 3a:

[0050] 0.2 mmol (0.060 g) of compound 1a, 0.2 mmol (0.062 g) of diphenyldiselenide 2a and 0.4 mmol of tetrabutylammonium tetrafluoroborate (0.132 g) were dissolved in acetonitrile (8 mL) to obtain a homogeneous solution A , added to syringe pump a; the injection flow rate of syringe pump a is 450μL / min; the applied current is 15mA; the microchannel reactor reaction volume V=225μL, and the reaction time is 30s; In the reaction liquid, the yield of the product calculated by HPLC was 77%, and the product 3a was obtained after separation by column chromatography.

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Abstract

The invention discloses a method for continuously preparing isobenzofuran compounds by using a micro-channel reaction device. The method comprises the following steps: dissolving an ortho-vinyl sulfonamide compound 1, diselenide 2 and an electrolyte in a solvent to obtain a homogeneous solution; pumping the homogeneous solution into the micro-channel reaction device, and carrying out a continuouselectrolytic reaction to obtain the isobenzofuran compound 3. The micro-channel reaction device is a micro-channel reaction device provided with an electrode. Compared with the prior art, the method has the following advantages: the micro-channel reaction device is adopted, so the reaction time is short, the product yield is high, and the reaction efficiency is remarkably improved; and meanwhile,expensive organic catalysts or metal catalysts do not need to be added, so operation is easy and convenient, environment friendliness and high efficiency are achieved, and cost is low.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for continuously preparing isobenzofuran compounds by using a microchannel reaction device. Background technique [0002] Isobenzofuran is an important class of heterocyclic compounds. Its derivative dihydroisobenzofuran is a synthetic precursor of isobenzofuran and other important heterocyclic derivatives. It has begun to be used as a synthetic intermediate to synthesize Biologically active compounds, such as phenolphthalein tablets that act on the colon, citalopram hydrobromide, an antidepressant, etc. At the same time, isobenzofuran is also an important raw material for the synthesis of biologically active substances and functional materials, especially isobenzofuran has a diene structure and can undergo Diels-Alder reaction, which enriches the application range of isobenzofuran in organic synthesis . [0003] At present, the methods for preparing isoben...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/02C07D307/87C25B11/04C25B11/12C25B3/23
CPCC07D307/87C25B11/04C25B3/23C25B11/043
Inventor 郭凯卞米雪方正花加伟刘成扣欧阳平凯
Owner NANJING TECH UNIV
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