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Method for preparing divinyl dipyridine compounds

A divinyl and bipyridine technology, applied in the field of preparation of divinyl bipyridine compounds, can solve the problems of low yield and short synthesis route, achieve good yield, easy separation, and avoid the use of highly toxic and dangerous drugs. effect used

Inactive Publication Date: 2012-01-04
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the yield is low, but it has the advantages of short synthetic route, easy operation and simple post-treatment.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] (1) Synthesis of 4,4'-dibromomethyl-2,2'-bipyridyl: in 300 milliliters of carbon tetrachloride, add 8 grams of 4,4'-dimethyl-2,2'-bipyridine Pyridine with 24 grams of N-bromosuccinimide (NBS), and 1 gram of azobisisobutyronitrile. Heated to reflux for 3 hours, cooled with ice water, and filtered to remove insoluble matter. The solvent was spun off to obtain light brown product 4,4'-dibromomethyl-2,2'-bipyridine 5.2 grams, yield 35%

[0012] (2) Synthesis of 4,4'-bis(diethylmethylphosphite)-2,2'-bipyridine (Wittig-Horner reagent): 6.8 grams of 4,4'-dibromomethyl-2 , 2'-bipyridyl and 60ml triethyl phosphite were mixed and stirred, refluxed for 4.5 hours and then cooled to room temperature. The unreacted triethyl phosphite was distilled off under reduced pressure, and the residue was refrigerated for 1 hour and then taken out, solidified into a dark brown solid, washed with 100 ml of ether, and dried under vacuum at 50 degrees Celsius to obtain 4,4'-bis( Diethylmethylph...

Embodiment 2

[0015] (1) Synthesis of 4,4'-dibromomethyl-2,2'-bipyridyl: in 400 milliliters of carbon tetrachloride, add 18.4 grams of 4,4'-dimethyl-2,2'-bipyridine Pyridine with 48 grams of N-bromosuccinimide (NBS), and 1 gram of azobisisobutyronitrile. Heated to reflux for 8 hours, cooled with ice water, and filtered to remove insoluble matter. The solvent was spun off to obtain brown product 4,4'-dibromomethyl-2,2'-bipyridine 12.6 grams, yield 37%

[0016] (2) Synthesis of 4,4'-bis(diethylmethylphosphite)-2,2'-bipyridine (Wittig-Horner reagent): 17.1 grams of 4,4'-dibromomethyl-2 , 2'-bipyridine was stirred with 90 ml of triethyl phosphite, heated to reflux, cooled to room temperature after 8 hours of reaction, unreacted triethyl phosphite was distilled off under reduced pressure, and the residue was placed in the refrigerator for 1 hour , solidified as a dark brown solid, washed with 150 milliliters of ether, and dried under vacuum at 50 degrees Celsius to obtain 19.4 grams of 4,4'-bi...

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Abstract

The invention relates to a method for preparing 4,4'-divinyl-2,2'-dipyridine. The method comprises: reacting 4,4'- dibromomethyl-2,2'-dipyridine with triethyl phosphate to obtain triethyl phosphate to obtain 4,4'-bis(diethylmethylphosphite)-2,2'-dipyridine (Wittig-Horner reagent); and performing the Horner-Emmons-Wadsworth reaction of the 4,4'-bis(diethylmethylphosphite)-2,2'-dipyridine and 37-percent formaldehyde solution to obtain4,4'-diethyl-2,2'-dipyridine. Compared with the prior art, the method has the characteristics of low raw material price, mild reaction conditions, easy product separation, simple and convenient operation, high yield and the like.

Description

technical field [0001] The invention relates to a chemical product and its preparation technology, in particular to a preparation method of divinyl bipyridine compounds. Background technique [0002] Metal complexes often attach to the surface of electrodes to form thin films through polymerization reactions, and undergo oxidation or reduction reactions. Research on new reactions and new ligand molecules that can be polymerized to form thin films has always been a hot area. Since Spiro and Ghosh first reported the preparation of 4-methyl-4'-divinyl-2,2'-bipyridine, this substance has become an important topic in the preparation of solid-phase catalysts and electroactive polymer films. Frequently used thickness and stable layers, in order to obtain sufficient thickness and stable layers, it is necessary to add compounds containing at least two electropolymerizable vinyl monomers to form complexes with central metal ions. In addition, this type of compound can also be used to...

Claims

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Application Information

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IPC IPC(8): C07D213/22
Inventor 齐东来代昭张庆印陈熙马明波
Owner TIANJIN POLYTECHNIC UNIV