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Preparation method of 2,4-dichloro-5-fluorobenzoyl chloride

A technology of fluorobenzoyl chloride and dichlorofluorobenzene, which is applied in the field of organic synthesis to achieve breakthroughs in technical bottlenecks, high yields, and less pollutant emissions

Active Publication Date: 2017-09-01
HEADING NANJING PHARMTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] In order to overcome the low utilization rate of the above-mentioned raw materials in the prior art and the shortcoming that the by-product dimer is produced, the present invention provides a method for further converting the dimer into 2,4-dichloro-5-benzoyl chloride , so that the conversion rate of raw materials is more than 80%, which has changed the shortcomings of difficult source of raw materials and low utilization rate, saves resources, reduces production costs, and is simple to operate and easy to scale up production

Method used

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  • Preparation method of 2,4-dichloro-5-fluorobenzoyl chloride
  • Preparation method of 2,4-dichloro-5-fluorobenzoyl chloride

Examples

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Effect test

Embodiment 1

[0041] Embodiment 1: a kind of preparation method of 2,4-dichloro-5-fluorobenzoyl chloride, total yield is 89.3%.

[0042]

[0043] The raw material 2,4-dichlorofluorobenzene (100g, 0.606mol) was added into carbon tetrachloride (107.4g, 0.667mol), after stirring and dissolving, iron trichloride (1.52g, 9.3mmol) was added, and the temperature was raised to Maintained at 70°C for 2 hours, the liquid phase detection raw materials basically disappeared. Cool down to room temperature, add 2.5M HClaq (500ml) to quench the reaction, stir until clarified and separate layers, take the lower organic phase and distill under reduced pressure to obtain compound I (128.5g, 75.1%) and compound III (25.3g, 20.3%).

[0044] 1 H NMR (CDCl 3 300MHz): δ7.548-7.646(d,1H),8.024-8.115(d,1H).

[0045]

[0046]Add anhydrous ferric chloride (1g) to compound I (20g, 70.9mmol), heat to 145°C, slowly add water (1.27g, 70.9mmol) dropwise, and continue stirring for 30 minutes after adding, the ga...

Embodiment 2

[0056] Embodiment 2: a kind of preparation method of 2,4-dichloro-5-fluorobenzoyl chloride, total yield is 92.1%

[0057] Step (1): The steps are the same as in Example 1, the difference lies in step (1), the step (1) of this example is to add the raw material 2,4-dichlorofluorobenzene (10g, 60.6mmol) to four After stirring and dissolving in carbon chloride (9.27g, 57.6mmol), chlorine trichloride (0.124g, 0.93mmol) was added, the temperature was raised to 40°C and maintained for 2 hours, and the liquid phase detection raw materials basically disappeared. Cool down to room temperature, add 2.5M HClaq (50ml) to quench the reaction, stir until clarified, separate layers, take the lower organic phase and distill under reduced pressure to obtain compound I (13.1g, 76.6%) and compound III (2.8g, 22.6%)

[0058] Step (2): The procedure is the same as in Example 1, adding anhydrous ferric chloride (2g) to compound I (40g, 141.8mmol), and after heating to 140°C, slowly add water (2.54...

Embodiment 3

[0062] Embodiment 3: A kind of preparation method of 2,4-dichloro-5-fluorobenzoyl chloride, the total yield is 88.5%

[0063] Step (1): Same as Example 1, add the raw material 2,4-dichlorofluorobenzene (100g, 0.606mol) into carbon tetrachloride (107.4g, 0.667mol), stir and dissolve, then add trichloride Iron (1.52g, 9.3mmol), the temperature was raised to 70°C and maintained for 2 hours, and the raw material basically disappeared in the liquid phase detection. Cool down to room temperature, add 2.5M HClaq (500ml) to quench the reaction, stir until clarified, then separate layers, take the lower organic phase and distill under reduced pressure to obtain compound I (128.5g, 75.1%) and compound III (25.3g, 20.3%).

[0064] Step (2): same as Example 1, the difference lies in step (2), the step (2) of the present embodiment joins anhydrous ferric chloride (3g) in compound I (30g, 106.3mmol) After heating to 145°C, water (1.52g, 101.0mmol) was slowly added dropwise, stirring was c...

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Abstract

The invention discloses a preparation method of 2,4-dichloro-5-fluorobenzoyl chloride and belongs to the field of organic synthesis. The preparation method comprises the following steps: with 2,4-dichlorofluorbenzene as a raw material, performing friedel-crafts reaction and hydrolyzation to generate an intermediate, 2,4-dichloro-5-fluorobenzoyl chloride; and hydrolyzing, oxidizing and acylating a byproduct, biopolymer (III), generated by the reaction to obtain a final compound (II), wherein the total yield is 88% or above. According to the invention, the raw material conversation ratio is 80% or above, the defects that existing raw materials are hardly available, and the utilization ratio is low are overcome, resources are saved, the production cost is lowered, and the preparation method is simple to operate and easy for amplified production.

Description

[0001] Technical field: [0002] The invention belongs to the field of organic synthesis and relates to a method for preparing fluoroquinolone intermediate 2,4-dichloro-5-fluorobenzoyl chloride. [0003] Background technique: [0004] Quinolones are artificially synthesized antibacterial drugs containing 4-quinolone core as the basic structure. Since the advent of norfloxacin in the late 1970s, the research and development of the third generation of quinolones-fluoroquinolones has led to the development of antibacterial drugs. Many new drugs with clinical value emerged, such as ofloxacin, ciprofloxacin, romefloxacin, and fleroxacin, which became one of the main clinical anti-infective drugs, second only to cephalosporins and penicillins drug. The structural characteristics of fluoroquinolones are that there is a fluorine atom at the 6-position and a substituted amino group at the 7-position. There are many synthetic routes reported in the literature, but the sources of these r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/58C07C63/70
CPCC07C17/269C07C45/43C07C51/16C07C51/285C07C51/305C07C51/58C07C63/70C07C25/13C07C25/18C07C49/813
Inventor 李文森
Owner HEADING NANJING PHARMTECH CO LTD
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