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Method for synthesizing diphenyl through Stille reaction recycling with organotin compound

A compound and organotin technology, applied in the field of organotin recycling application, can solve the problem of low utilization rate of organotin, achieve the effect of optimizing synthesis process conditions and effective separation and utilization

Active Publication Date: 2015-11-04
JIANGSU SAILBOAT PETROCHEMICAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The purpose of the present invention is to solve the problem of the low utilization rate of organotin in the preparation of biphenyl compounds by the existing Stille method, and provide a method for synthesizing biphenyl by stille reaction of organotin compounds

Method used

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  • Method for synthesizing diphenyl through Stille reaction recycling with organotin compound
  • Method for synthesizing diphenyl through Stille reaction recycling with organotin compound
  • Method for synthesizing diphenyl through Stille reaction recycling with organotin compound

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specific Embodiment approach 1

[0035] Specific embodiment one: the method for synthesizing biphenyl by Stille reaction of organotin compound recycling in this embodiment is implemented according to the following steps:

[0036] 1. Add metal magnesium chips and bromobenzene into a three-necked flask with a constant pressure dropping funnel and a drying tube, replace with nitrogen three times, heat and reflux for 1.5-2.5 hours, cool to room temperature, place in an ice-water bath, and add dropwise Tributyltin chloride tetrahydrofuran mixed solution, gray-white precipitate was obtained, and then continued to reflux for 12-14 hours, then added saturated ammonium chloride solution, extracted with ether, dried with anhydrous magnesium sulfate, removed impurities, and obtained light yellow liquid by suction filtration. After vacuum distillation, the cuts were collected to obtain a colorless solution of tributylphenyltin (M R = 364.13);

[0037]2. Use a syringe to inject halobenzene, tributylphenyl tin, cuprous io...

specific Embodiment approach 2

[0042] Specific embodiment 2: The difference between this embodiment and specific embodiment 1 is that in step 1, the material ratio of metal magnesium chips, bromobenzene and tributyltin chloride is 1.0:1.0:1.0-1.1. Other steps and parameters are the same as those in Embodiment 1.

specific Embodiment approach 3

[0043] Specific embodiment three: the difference between this embodiment and specific embodiment one or two is that in step one, metal magnesium chips and bromobenzene are added to a three-necked flask with a constant pressure dropping funnel and a drying tube, and nitrogen is replaced three times. Heat to reflux at ~45°C for 1.5~2.5h. Other steps and parameters are the same as those in Embodiment 1 or Embodiment 2.

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Abstract

The invention provides a method for synthesizing diphenyl through Stille reaction recycling with an organotin compound, and relates to a method for preparing diphenyl through a Stille reaction. A purpose of the present invention is to solve the problem of low organotin utilization rate of the existing Stille method for preparing the diphenyl compound. The method comprises: 1, adopting tri-butyltin chloride and bromobenzene as raw materials, and carrying out a reaction under the effect of a Grignard reagent to synthesize tributylphenyltin; 2, carrying out a reaction of a mixed solution of halogenated benzene, tributylphenyltin, cuprous iodide, lithium chloride, palladium(triphenylphosphine)dichloride and cesium fluoride DMF to prepare diphenyl, and collecting the filter residue; 3, dissolving the filter residue with acetone, dissolving the insoluble matter with absolute alcohol, and concentrating to obtain fluorotributyltin; and 4, converting the tin fluoride into the organic tin chloride with saturated ammonium chloride tetrahydrofuran. According to the present invention, the synthesis process conditions are optimized, the highest yield of the diphenyl compound achieves 97%, and the effective separation utilization of the organic tin chloride is achieved.

Description

technical field [0001] The invention relates to a method for recycling organotin in the process of preparing biphenyl by Stille reaction. Background technique [0002] The formation of carbon-carbon bonds has been a very hot topic in the past ten years, and the SP 2 Hybrid carbon-carbon bond synthesis is a new challenge in organic synthesis today. Wherein the biphenyl compound is a representative class of compounds, and its basic skeleton is formed by connecting two phenyl groups, and its simplest representative is exactly biphenyl (chemical formula: C 12 h 10 ). Its derivatives include benzidine, diphenyl ether, octabromodiphenyl ether, polychlorinated biphenyls, etc. [0003] Biphenyl compounds are ubiquitous in many natural products with physiological functions and pharmaceutical intermediates. As organic precursors, biphenyl compounds are widely used in the fields of drug synthesis, fine chemicals, and polymers. Therefore, the research on the synthesis method of bip...

Claims

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Application Information

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IPC IPC(8): C07C15/14C07C1/32
Inventor 宋伟明孙立柏薇薇李世兴邓启刚
Owner JIANGSU SAILBOAT PETROCHEMICAL CO LTD
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