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Preparation method of alpha-bromoacetyl ferrocene

A technology of bromoacetyl ferrocene and acetyl ferrocene, which is applied in the field of preparation of α-bromoacetyl ferrocene, can solve the problems of difficult synthesis, difficult post-processing, harsh conditions, etc., and achieve simple post-processing, The effect of preventing the solvent from evaporating too much and reacting quickly

Inactive Publication Date: 2013-09-11
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The main synthetic methods of this compound are ① acetyl ferrocene and NBS (N-bromosuccinimide) in LDA, Me 3 The reaction of SiCl and THF at -78°C; ②The reaction of acetyl ferrocene and bromine water at 0°C under the catalysis of HBr; ③The Friedel-Crafts reaction of ferrocene and bromoacetyl bromide, but the reactions are all at low temperature Reaction, harsh conditions, and difficult post-processing, these shortcomings make it difficult to synthesize α-bromoacetyl ferrocene in the laboratory

Method used

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  • Preparation method of alpha-bromoacetyl ferrocene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] 1) Add 0.001mol of acetylferrocene, 0.0011mol of N-bromosuccinimide and 12mL of ethanol to the crucible, stir well and dissolve to obtain a reaction solution;

[0020] 2) Put the crucible containing the reaction solution in a microwave oven, adjust to 750W, turn on the microwave reaction, irradiate the crucible with the reaction solution in the microwave oven for 5 seconds, turn off the microwave oven, take out the microwave oven and stir to cool down for 10 seconds, repeat the radiation-take out the microwave oven The process of stirring and cooling until the TLC detects that the acetyl ferrocene raw material point disappears, the reaction is stopped, and the reaction system is obtained in the crucible; wherein, the developing agent of TLC is a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:3 made;

[0021] 3) Distill off the ethanol in the reaction system to obtain a solid, wash the solid with petroleum ether until the filtrate is colorless to r...

Embodiment 2

[0023] 1) Add 0.002mol of acetylferrocene, 0.0026mol of N-bromosuccinimide and 30mL of acetonitrile into the crucible, stir well and dissolve to obtain a reaction solution;

[0024] 2) Put the crucible containing the reaction solution in a microwave oven, adjust to 750W, turn on the microwave reaction, irradiate the crucible with the reaction solution in the microwave oven for 5 seconds, turn off the microwave oven, take out the microwave oven and stir to cool down for 10 seconds, repeat the radiation-take out the microwave oven The process of stirring and cooling until the TLC detects that the acetyl ferrocene raw material point disappears, the reaction is stopped, and the reaction system is obtained in the crucible; wherein, the developing agent of TLC is a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:3 made;

[0025] 3) Distill off the acetonitrile in the reaction system to obtain a solid, wash the solid with petroleum ether until the filtrate is co...

Embodiment 3

[0027] 1) Add 0.002mol of acetylferrocene, 0.0024mol of N-bromosuccinimide and 48mL of methanol into the crucible, stir well and dissolve to obtain a reaction solution;

[0028] 2) Put the crucible containing the reaction solution in a microwave oven, adjust to 750W, turn on the microwave reaction, irradiate the crucible with the reaction solution in the microwave oven for 5 seconds, turn off the microwave oven, take out the microwave oven and stir to cool down for 10 seconds, repeat the radiation-take out the microwave oven The process of stirring and cooling until the TLC detects that the acetyl ferrocene raw material point disappears, the reaction is stopped, and the reaction system is obtained in the crucible; wherein, the developing agent of TLC is a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:3 made;

[0029] 3) Distill the methanol in the reaction system, wash the solid with petroleum ether until the filtrate is colorless to remove traces of un...

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Abstract

The invention discloses a preparation method of alpha-bromoacetyl ferrocene. The method comprises the following steps: by using acetyl ferrocene and N-bromo succinimide as a reaction raw material, adding a solvent to uniformly mix; radiating by microwave; stirring; evaporating the solvent after reaction; washing by hot water; and filtering and drying to obtain red brown particle solids to obtain the target product alpha-bromoacetyl ferrocene. The preparation method disclosed by the invention under microwave radiation assisted condition is quick to react, simple and convenient to operate, simple in post-treatment, high in yield and easy to implement, and alpha-bromoacetyl ferrocene can be efficiently and quickly synthesized. The defect that the original alpha-bromoacetyl ferrocene process is severe in reaction condition and the raw materials are not easy to get is overcome.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a preparation method of α-bromoacetyl ferrocene. Background technique [0002] Ferrocene derivatives are hydrophobic, can pass through the cell membrane smoothly, and act with various enzymes, DNA, RNA and other substances in the cell, so they may be used as drugs for the treatment of certain diseases. α-Bromoacetyl ferrocene (CAS No: 111974-27-7, molecular formula: C 12 h 11 BrFeO) has broad application prospects in biology, medicine, microbiology and other fields because of its easy introduction of ferrocene groups into other active units. [0003] The structural formula of α-bromoacetylferrocene is shown below: [0004] [0005] The main synthetic methods of this compound are ① acetyl ferrocene and NBS (N-bromosuccinimide) in LDA, Me 3 The reaction of SiCl and THF at -78°C; ②The reaction of acetyl ferrocene and bromine water at 0°C under the catalysis of HB...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
Inventor 刘玉婷梁钢涛尹大伟张韩利李鑫吕博
Owner SHAANXI UNIV OF SCI & TECH
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