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Synthesis method of intermediate bis(carboxylcyclopentadiene)iron

A technology of cyclopentadiene, synthesis method, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve the problem of slow reaction, low yield and limited large-scale industrial application and other issues

Inactive Publication Date: 2020-07-07
徐州顺平生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Traditional methods are difficult to balance in terms of yield, by-products and controllability. There are generally disadvantages such as low yield, slow reaction, and expensive catalysts, which limit its large-scale industrial application.

Method used

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  • Synthesis method of intermediate bis(carboxylcyclopentadiene)iron

Examples

Experimental program
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Embodiment 1

[0018] 1. A synthetic method for intermediate bis(carboxycyclopentadiene)iron, characterized in that the method comprises the following steps:

[0019] Step 1. Dissolve 1mol of 1,1'-diacetylferrocene and 2.5mol of cuprous chloride in 350ml of [C 5 mim]HSO 4 In the ionic liquid, after stirring and reacting at 50°C for 1h, the temperature was raised to 95°C and then stirred for 1h;

[0020] Step 2. After cooling, add 150ml of [C 5 mim]HSO 4 The ionic liquid is continuously stirred at a certain temperature, and the solution of the product is obtained after the reaction is completed;

[0021] Step 3, filter the solution of the product while it is hot, and the filtrate is acidified to pH=2 with concentrated hydrochloric acid, a large amount of yellow precipitates are formed, and the crude product is obtained after suction filtration;

[0022] Step 4, put the obtained product in a beaker, add 10% NaOH solution to dissolve all the product;

[0023] Step 5, filter the solution, a...

Embodiment 2

[0031] Step 1. Dissolve 0.8mol of 1,1'-diacetylferrocene and 2.5mol of cuprous chloride in 350ml of [C 5 mim]HSO 4 In the ionic liquid, after stirring and reacting at 50° C. for 1 h, the temperature was raised to 95° C. and then stirred for 1 h; the rest of the steps were the same as in Example 1.

Embodiment 3

[0033] Step 1. Dissolve 0.6mol of 1,1'-diacetylferrocene and 2.5mol of cuprous chloride in 350ml of [C 5 mim]HSO 4 In the ionic liquid, after stirring and reacting at 50° C. for 1 h, the temperature was raised to 95° C. and then stirred for 1 h; the rest of the steps were the same as in Example 1.

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Abstract

The invention discloses a synthesis method of bis(carboxylcyclopentadiene)iron, which comprises the following steps: 1,1'-diacetyl ferrocene, cuprous chloride, N-methylimidazole, toluene, butane, brominated 1-amyl-methylimidazole and concentrated sulfuric acid are used as main raw materials; according to the synthesis process disclosed by the invention, self-made [C5mim]HSO4 ionic liquid is used as a reaction solvent, so that the bis(carboxylcyclopentadiene)iron is prepared through catalysis of a uniformly dispersed oxidation system formed by CuCl and an ionic liquid, and therefore, catalyticoxidation of diacetyl ferrocene in a short time can be realized, and high catalytic activity and selectivity are shown.

Description

technical field [0001] The invention relates to a method for synthesizing an intermediate bis(carboxycyclopentadiene)iron, belonging to the field of chemical synthesis. Background technique [0002] Bis(carboxycyclopentadienyl) Iron (Bis(carboxycyclopentadienyl) Iron) CAS: 1293-87-4 belongs to ferrocene derivatives and has various biological activities. Certain effects, and the introduction of penicillin, cephalosporin, and trihydrocarbyl tin can improve the antibacterial performance of the compound, and even endow the compound with plant growth regulation. The current synthetic method is mainly to acylate ferrocene into acetyl ferrocene, and then react with sodium hypochlorite to produce bis(carboxycyclopentadiene)iron; or react ferrocene with o-chlorobenzoyl chloride, Produce o-chlorobenzoyl ferrocene, and then react with potassium tert-butoxide to produce bis(carboxycyclopentadiene)iron. Traditional methods are difficult to balance yield, by-products and controllability...

Claims

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Application Information

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IPC IPC(8): C07F17/02C07D233/56B01J31/30
CPCB01J31/30C07D233/56C07F17/02Y02P20/54
Inventor 赵可王明
Owner 徐州顺平生物科技有限公司
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