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Synthesis method of 3-bromo-4-fluorobenzaldehyde

A technology of fluorobenzaldehyde and synthesis method, which is applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of high environmental hazards and high risks, and achieve green processes, low risks, and high yields. high rate effect

Active Publication Date: 2019-06-21
SINOPHARM CHEM REAGENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The object of the present invention is to provide a kind of synthetic method of 3-bromo-4-fluorobenzaldehyde, to solve the problem that the synthetic raw material in the prior art involves the precursor chemical bromine or highly toxic chlorine, high risk and great environmental hazards Waiting question

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  • Synthesis method of 3-bromo-4-fluorobenzaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0025] A kind of synthetic method of 3-bromo-4-fluorobenzaldehyde, comprises the following steps:

[0026] (1) 1mol of 4-fluorobenzaldehyde was dissolved in 160mL of dichloromethane to obtain solution A;

[0027] (2) Dissolve 1.01 mol of sodium bromide in 100 mL of pure water, and add 100 mL of 35% hydrochloric acid under stirring to obtain solution B;

[0028] (3) At 20-25°C, after mixing solution A and solution B, turn on the ultrasonic wave, and add 1.02mol of 8% sodium hypochlorite aqueous solution dropwise within 1 hour under stirring;

[0029] (4) dropwise addition is completed, heat preservation 30 minutes under ultrasonic, stirring; Then stand still for 15 minutes;

[0030] (5) phase separation, dichloromethane phase washing to neutrality, drying and precipitation;

[0031] (6) The crude product was obtained, and the bulk melted and crystallized at 31°C to obtain the pure product.

[0032] Finally, 185 g of pure product was obtained, with a purity of 99.2% and a yie...

Embodiment 2

[0034] A kind of synthetic method of 3-bromo-4-fluorobenzaldehyde, comprises the following steps:

[0035] (1) 1mol of 4-fluorobenzaldehyde was dissolved in 140mL of dichloromethane to obtain solution A;

[0036] (2) Dissolve 1.03 mol of sodium bromide in 110 mL of pure water, and add 110 mL of 35% hydrochloric acid under stirring to obtain solution B;

[0037] (3) At 20-25°C, after mixing solution A and solution B, turn on the ultrasonic wave, and add 1.03mol 8% sodium hypochlorite aqueous solution dropwise within 1 hour under stirring;

[0038] (4) dropwise addition is completed, heat preservation 30 minutes under ultrasonic, stirring; Then stand still for 15 minutes;

[0039] (5) phase separation, dichloromethane phase washing to neutrality, drying and precipitation;

[0040] (6) The crude product was obtained, and the bulk melted and crystallized at 31°C to obtain the pure product.

[0041] Finally, 187.7 g of pure product was obtained, with a purity of 99.4% and a yiel...

Embodiment 3

[0043] A kind of synthetic method of 3-bromo-4-fluorobenzaldehyde, comprises the following steps:

[0044] (1) 1mol of 4-fluorobenzaldehyde was dissolved in 160mL of dichloromethane to obtain solution A;

[0045] (2) Dissolve 1 mol of sodium bromide in 90 mL of pure water, and add 90 mL of 35% hydrochloric acid under stirring to obtain solution B;

[0046] (3) At 20-25°C, after mixing solution A and solution B, turn on the ultrasonic wave, and add 1.04mol 8% sodium hypochlorite aqueous solution dropwise within 1 hour under stirring;

[0047] (4) dropwise addition is completed, heat preservation 30 minutes under ultrasonic, stirring; Then stand still for 15 minutes;

[0048] (5) phase separation, dichloromethane phase washing to neutrality, drying and precipitation;

[0049] (6) The crude product was obtained, and the bulk melted and crystallized at 31°C to obtain the pure product.

[0050] Finally, 183.6 g of pure product was obtained, with a purity of 99.2% and a yield of ...

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Abstract

The invention relates to the technical field of synthesis of pesticide and pharmaceutical intermediates, in particular to a synthesis method of 3-bromo-4-fluorobenzaldehyde. The method comprises following steps: (1), 4-fluorobenzaldehyde is dissolved in dichloromethane, and a solution A is obtained; (2), sodium bromide is dissolved in pure water, 35% hydrochloric acid is added during stirring, anda solution B is obtained; (3), after the solution A and the solution B are mixed, ultrasonic waves are started, and an aqueous sodium hypochlorite solution is dropwise added during stirring; (4), after the aqueous sodium hypochlorite solution is dropwise added, thermal insulation is performed under the ultrasonic and stirring condition, and then the solution is left to stand; (5), phase splittingis performed, a methylene dichloride phase is washed to be neutral, and drying and desolvation are performed; (6), a crude product is obtained, body melt crystallization is performed at 31 DEG C, anda pure product is obtained. According to the synthesis method, a catalyst is not needed, and precursor chemical bromine or highly toxic chlorine is not involved in the process; the raw materials areeasily available, dangerousness is lower, and the yield is high; the process is green, easy to operate and environmentally friendly.

Description

technical field [0001] The invention relates to the field of synthesis of pesticide and pharmaceutical intermediates, in particular to a synthesis method of 3-bromo-4-fluorobenzaldehyde. Background technique [0002] 3-Bromo-4-fluorobenzaldehyde is an organic compound with the formula C 7 h 4 BrFO is used for chemical reagents, pesticide and pharmaceutical intermediates (such as: bifenthrin, the main intermediate of flufenthrin) and synthetic building blocks. [0003] At present, the preparation method adopted in the traditional technology is to dissolve p-fluorobenzaldehyde in a solvent, add bromine dropwise at a certain temperature, react for 1-2 hours after the dropwise addition, and then precipitate to obtain the product. [0004] In addition, CN1508124 (a method for synthesizing cyfluthrin with p-fluorobenzaldehyde) discloses taking p-fluorobenzaldehyde as a raw material, adding bromine (liquid bromine) and chlorine, and using aluminum trichloride as a catalyst to car...

Claims

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Application Information

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IPC IPC(8): C07C47/55C07C45/63
Inventor 吴孝兰郭建国凌芳陆慧懿
Owner SINOPHARM CHEM REAGENT
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