Preparation method of phenyl sulfide compound

A compound, phenylene sulfide technology, applied in the field of preparation of phenylene sulfide compounds, can solve the problems of rare transition metals, pollution, metal reagent residues, etc.

Pending Publication Date: 2021-11-16
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing technology uses transition metals to catalyze the coupling reaction, so that the C-S cross-coupling can be easily completed in one step. However, the transition metals are rare and expensive, and the metal reagents remain after the reaction and the pollution problem is prominent.
Obviously, metal-free C-S coupling synthesis of thioethers is more attractive to researchers; however, the existing schemes usually require harsh conditions such as strong base / high temperature, strong oxidant, Grignard reagent, or pre-prepared diazonium salt, iodonium , sulfonium and other precursors, the operation is troublesome

Method used

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  • Preparation method of phenyl sulfide compound
  • Preparation method of phenyl sulfide compound
  • Preparation method of phenyl sulfide compound

Examples

Experimental program
Comparison scheme
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Synthetic example

[0029]

[0030] At room temperature, NaH (0.9 mmol, 3.0 equiv) was weighed in a reaction flask, suspended in anhydrous THF (0.8 mL) with conventional magnetic stirring, and thiophenol 1 (0.3 mmol, 1.0 equiv, dissolved in 0.2 mL DMA), stirred at room temperature for 2 min after the addition, then added diiodobenzene 2a (0.6 mmol, 2.0 equiv, dissolved in 0.2 mL THF), continued to stir at room temperature, and monitored the reaction by TLC. After the reaction is complete, add ice water and tetrahydrofuran to quench the reaction, extract three times with ethyl acetate, combine the organic layers, wash with saturated NaCl solution, dry over anhydrous sodium sulfate, filter, spin to dry the solvent, add silica gel powder to mix the sample, and quickly column layer Analysis and separation, the product iodine-containing phenylene sulfide 3 was obtained, and the yield was conventionally calculated.

[0031] Under the above-mentioned preparation method, thiophenol 1 with different st...

Embodiment

[0050]

[0051] Coupling reaction of phenylboronic acid with iodine-containing phenylene sulfide:

[0052]

[0053] in N 2 Under protection, iodine-containing diphenylsulfide (0.3 mmol, 1.0 equiv), phenylboronic acid (0.45 mmol, 1.5 equiv), Pd(PPh 3 ) 4 (0.03 mmol, 10 mol%), K 2 CO 3 (0.9 mmol, 3.0 equiv) was weighed into a two-necked flask, 2 mL of DMF was added, heated at 60°C for 30 min, and then the temperature was raised to 120°C for conventional stirring reaction, and the reaction was monitored by TLC. After 5 h, the raw materials were consumed. After the reaction solution was cooled to room temperature, water was added, ethyl acetate was extracted 4 times, washed 2 times with water, the organic layers were combined, washed with saturated NaCl solution, dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated by rotary evaporation. The sample was mixed with silica gel powder, separated by flash column chromatography (pure PE), and the oily ...

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Abstract

The invention discloses a preparation method of a phenyl sulfide compound, which comprises the following steps: by taking thiophenol and o-diiodobenzene as substrates, reacting in a solvent in the presence of a metal hydride to obtain iodine-containing phenyl sulfide; the iodine-containing phenyl sulfide can be subjected to intramolecular reaction to obtain a phenyl sulfide compound; or the iodine-containing phenyl sulfide can react with other raw materials to obtain the phenyl sulfide compound. The ortho-iodine compound prepared by the invention has great application value, can be further widely converted, can be subjected to coupling reaction with phenylboronic acid, thiophenol, phenylacetylene and the like under the catalysis of Pd to prepare various 2-substituted thiophenol, and has important significance in material science and pharmaceutical synthesis.

Description

technical field [0001] The invention belongs to organic synthesis, and in particular relates to a preparation method of phenylene sulfide compound. Background technique [0002] The phenylene sulfide structure widely exists in various active natural medicines and functional materials. The study of the synthesis of thioether compounds has always been the eternal goal of chemists, which is of great significance for the development of innovative drugs and the discovery of new materials. The existing technology uses transition metals to catalyze the coupling reaction, so that the C-S cross-coupling can be easily completed in one step. However, the transition metals are rare and expensive, and the metal reagents remain after the reaction, causing serious pollution problems. Obviously, metal-free C-S coupling synthesis of thioethers is more attractive to researchers; however, the existing schemes usually require harsh conditions such as strong base / high temperature, strong oxidizi...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C323/09C07C323/62C07C323/20C07D295/096C07D333/76
CPCC07C319/14C07C319/20C07D295/096C07D333/76C07C323/09C07C323/62C07C323/20
Inventor 张士磊胡敏祝文静姜远锐方春辉陈鑫黄加文胡延维
Owner SUZHOU UNIV
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