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Synthesis method of novel compound 4,4'-bis(trimethylsilyl)-2,2'-bipyridyl

A technology based on trimethylsilyl and trimethylsilane, which is applied in the field of new compound 4, can solve problems such as reporting and no synthetic route, and achieve the effects of cheap materials, easy availability of materials, and superior product performance

Inactive Publication Date: 2012-08-29
JIANGNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] 4,4'-bis(trimethylsilyl)-2,2'-bipyridine, as a new type of compound, has no specific synthetic route report, only the relevant report of trimethylsilation reaction

Method used

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  • Synthesis method of novel compound 4,4'-bis(trimethylsilyl)-2,2'-bipyridyl
  • Synthesis method of novel compound 4,4'-bis(trimethylsilyl)-2,2'-bipyridyl

Examples

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Effect test

Embodiment 1

[0021] Embodiment 1: Compound 4, the synthesis of 4'-bis(trimethylsilyl)-2,2'-bipyridine

[0022] Add 20g of 2,2′-bipyridine and 120mL of glacial acetic acid into a 500mL three-necked round-bottom flask, start the stirrer to stir and dissolve; after it is completely dissolved, add 30ml of hydrogen peroxide (mass fraction 30%), pass condensed water and heat with an oil bath , control the temperature of the oil bath in the range of 78-82°C, heat and stir; the reaction lasts for 48 hours. Add 20ml of hydrogen peroxide (mass fraction 30%) every 6 hours, and control the temperature at about 80°C; after the reaction stops, it is cooled to room temperature, and the mixed solution is rotary evaporated with a rotary evaporator to evaporate most of the solvent, and then Dilute with water, continue rotary evaporation, take out the remaining acetic acid. After repeating three times, the solution was basically neutral, and after evaporating to dryness, a light yellow solid was obtained fo...

Embodiment 2

[0031] Embodiment 2: Compound 4, the synthesis of 4'-bis(trimethylsilyl)-2,2'-bipyridine

[0032] The method for synthesizing 4,4'-dibromo-2,2'-bipyridine is as described in Example 1.

[0033] Add 0.5g metal sodium (22mmol) and 15ml methanol in a 50ml three-necked flask, start stirring, distill off excess methanol after all the sodium reaction is over, and then evaporate it to dryness with reduced pressure distillation to obtain 1g of white powdery solid, namely It is sodium methoxide, stand-by; weigh 200mg of prepared sodium methoxide (4mmol), add it to a 25ml single-necked flask, put it into a stirring bar, seal it with a rubber stopper, and coat the seal with vaseline; measure 2.5ml hexamethylphosphine with a syringe Pour triamide (HMPT) into the flask, start the stirrer to stir; install the exhaust device, use the oil pump and double-row pipe to get rid of the air in the flask and the dissolved oxygen in the solvent and nitrogen, repeat 3 times before and after That is t...

Embodiment 3

[0034] Embodiment 3: Compound 4, the synthesis of 4'-bis(trimethylsilyl)-2,2'-bipyridine

[0035] The method for synthesizing 4,4'-dibromo-2,2'-bipyridine is as described in Example 1.

[0036] Add 0.5g metallic sodium (22mmol) and 15ml ethanol in the 50ml three-necked flask, start stirring, distill off excess ethanol after all the reactions of sodium are finished, then evaporate it to dryness with reduced pressure distillation, obtain white powdery solid 1.15g, It is sodium ethylate, stand-by; weigh 163mg of prepared sodium ethylate (2.4mmol), add it to a 25ml single-necked flask, put it into a stirrer and seal it with a rubber stopper, and coat the seal with vaseline; measure 5ml hexamethyl alcohol with a syringe After injecting phosphoric triamide (HMPT) into the flask, start the stirrer to stir; install the exhaust device, use the oil pump and double-row pipe to remove the air in the flask and the dissolved oxygen in the solvent and introduce nitrogen, repeat 3 times befor...

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Abstract

The invention belongs to the technical field of organic synthesis and particularly relates to a synthesis method of novel compound 4,4'-bis(trimethylsilyl)-2,2'-bipyridyl. According to the synthesis method, 2,2'-dipyridyl is utilized as an original raw material. The synthesis method comprises the following steps of: oxidation reaction: oxidating 2,2'-dipyridyl by utilizing an oxidizer, so as to generate a 2,2'-dipyridyl N,N'-oxide; nitration reaction: nitrating the 2,2'-dipyridyl N,N'-oxide in sulfuric acid by virtue of fuming nitric acid, so as to generate 4,4'-binitro-2,2'-dipyridyl N,N'-oxide; bromination reaction: performing bromine substitution reaction on the 4,4'-binitro-2,2'-dipyridyl N,N'-oxide in the presence of a brominating agent under an acid environment, so as to generate 4,4'-dibromo-2,2'-dipyridyl N,N'-oxide; deoxidation reaction: enabling the 4,4'-dibromo-2,2'-dipyridyl N,N'-oxide and phosphorus tribromide to react in a solvent, so as to generate 4,4'-dibromo-2,2'-dipyridyl; and trimethyl silicification reaction: enabling the 4,4'-dibromo-2,2'-dipyridyl and a trimethyl silanion solution to react, so as to obtain the 4,4'-bis(trimethylsilyl)-2,2'-bipyridyl. The synthesis method provided by invention has the advantages that the operation is simple, used materials are cheap and easily available, the yield is higher, the product purity is high, the product performance is excellent, and the method is better in development prospect and application potential.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of a novel compound 4,4'-bis(trimethylsilyl)-2,2'-bipyridine. Background technique [0002] 2,2′-bipyridine and its derivatives have R electron-donating ability and P electron-accepting ability. As an excellent N-type electron-donating ligand, it can form complexes with most transition metals in a wide range. These coordination Objects often have novel structures or special properties. The optoelectronic properties of the complex are closely related to the substituents on the ligand. These bipyridine complexes can be adjusted by selecting electron-withdrawing or electron-donating groups at different positions on the 2,2'-bipyridine ligand. The properties of ground state and excited state of matter make it develop in the direction that people need. The substituent at the 4,4'-position not only has a simple synthesis method, but also makes...

Claims

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Application Information

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IPC IPC(8): C07F7/10
Inventor 郑昌戈宋阳杨茂志
Owner JIANGNAN UNIV
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