A kind of preparation method of 2-fluoro-5-formyl chloride pyridine

A technology of formyl chloride pyridine and picoline, which is applied in the field of preparation of 2-fluoro-5-formyl chloride pyridine, can solve the problems that there is no very mature process technology report, and achieve the effect of low production cost and high conversion rate

Active Publication Date: 2022-03-04
内蒙古佳瑞米精细化工有限公司
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AI-Extracted Technical Summary

Problems solved by technology

[0003] At present, only reagent companies in the domestic market provide a small amount of samples, and the puri...
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Abstract

The invention relates to a preparation method of 2-fluoro-5-formyl chloride pyridine, which belongs to the technical field of organic chemistry. The method steps are: 1) using 2-fluoro-5-picoline as a raw material, reacting in the presence of potassium permanganate or sodium permanganate to obtain 2-fluoro-5-picoic acid pyridine; 2) using 2- Fluoro-5-formyl pyridinium and thionyl chloride or oxalyl chloride are refluxed in a chlorinated solvent. After the reaction is over, after the solvent is distilled under reduced pressure, add an alkane solvent to freeze and filter to obtain a 2-fluoro-5-formyl chloride pyridine solution. Rectification under reduced pressure gives 2-fluoro-5-formyl chloride pyridine. The invention has the advantages of high conversion rate, the purity of the obtained product is as high as 99.0 percent, the purity of the product is less than 0.5 percent, the production cost is low, and it is suitable for industrialized production.

Application Domain

Organic chemistry

Technology Topic

Sodium permanganateFormic acid +8

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  • A kind of preparation method of 2-fluoro-5-formyl chloride pyridine

Examples

  • Experimental program(5)

Example Embodiment

[0024] Example 1:
[0025] In a 500 ml three-mouth flask, 11.1 g (0.1 mol) 2-fluoro-5-methylpyridine was added, and 250 ml of water was added, and the mechanical stirring was activated, and 31.6 g (0.2 mol) of KMNO was sequentially added. 4 And 5.6 g (0.1 mol) KOH, the oil bath was heated to 95 ° C, the reaction was 5 h, filtered through heat, and the filtrate was collected. After the filtrate was reduced to normal temperature, the pH is adjusted to 2 to 4, and there is solid precipitation, filtration; the filtrate is extracted twice with dichloroethane. The filtered solid and the extracted oil phase were mixed, and the evaporation was evaporated to give a white solid 11.8 g, that is, 2-fluoro-5-formate pyridine (melting point 275 to 278 ° C).
[0026] The 2-fluoro-5-formate obtained by the first step was put into 500 ml of three bottles, 200 ml of dichloromethane, start stirring, dripping 6 h, reflux reaction for 6 h, evaporated, excess 2 Chloride. After adding n-heptane 80 mL, it is reduced to close filtration, and the filtrate is reduced pressure. It has a purity of 99.0%, and the total yield is 80.1%.

Example Embodiment

[0027] Example 2:
[0028] In the 500 ml three-mouth flask, 11.1 g (0.1 mol) 2-fluoro-5-methylpyridine was added, and 250 ml of water was added, and the mechanical stirring was activated, and 28.4 g (0.2 mol) namno was sequentially added. 4 And 4.0 g (0.1 mol) NaOH, the oil bath was heated to 95 ° C, the reaction was 5 h, filtered through heat, and the filtrate was collected. After the filtrate was reduced to normal temperature, the pH is adjusted to 2 to 4, and there is solid precipitation, filtration; the filtrate is extracted twice with dichloroethane. The filtered solid and extracted oil phase were mixed, and the evaporation was evaporated to give a white solid 11.5 g, which is 2-fluoro-5-formate pyridine (melting point 275 to 278 ° C).
[0029] Other steps were in Example 1, 2-fluoro-5-formyl chloride pyridine was obtained, and the purity was 99.0%, and the total yield was 78.7%.

Example Embodiment

[0030] Example 3:
[0031] In a 500 ml three-mouth flask, 11.1 g (0.1 mol) 2-fluoro-5-methylpyridine was added, 250 ml of water, was allowed to activate the mechanical stirring, and 47.4 g (0.3 mol) of KMNO was sequentially added. 4 And 5.6 g (0.1 mol) KOH, the oil bath was heated to 95 ° C, the reaction was 5 h, filtered through heat, and the filtrate was collected. After the filtrate was reduced to normal temperature, the pH is adjusted to 2 to 4, and there is solid precipitation, filtration; the filtrate is extracted twice with dichloroethane. The filtered solid and extracted oil phase were mixed, and the evaporation was evaporated to give a white solid 12.1 g, which is 2-fluoro-5-formate pyridine (melting point 275 to 278 ° C).
[0032] The 2-fluoro-5-formate obtained by the first step was put into 500 ml of three bottles, 200 ml of dichloromethane, start stirring, dripping 6 h, reflux reaction for 6 h, evaporated, excess 2 Chloride. The n-heptane was added to 85 ml, cooling and closed filtration, filtrate reduced pressure distillation, collected from 90 to 94 ° C / 15 mm Hg fraction to obtain a colorless liquid product 2-fluoro-5-formyl chloride pyridine 12.85 g, frozen for a white solid, It has a purity of 99.1%, and the total yield reaches 80.56%.

PUM

PropertyMeasurementUnit
Melting point275.0 ~ 278.0°C

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