A kind of synthetic method of 3-bromo-4-fluorobenzaldehyde

Abstract

The present invention relates to the synthetic technical field of pesticide pharmaceutical intermediates, especially a kind of synthetic method of 3-bromo-4-fluorobenzaldehyde, comprising the following steps: (1) dissolving 4-fluorobenzaldehyde in dichloromethane to obtain a solution A; (2) sodium bromide is dissolved in pure water, and 35% hydrochloric acid is added under stirring to obtain solution B; (3) after solution A and solution B are mixed, the ultrasonic wave is turned on, and sodium hypochlorite aqueous solution is added dropwise under stirring; (4 ) dropwise, keep warm under ultrasonication and stirring, and then stand still; (5) separate phases, wash the dichloromethane phase with water until neutral, dry and precipitate; The synthesis method does not need to use a catalyst, and the process does not involve the precursor chemical bromine or highly toxic chlorine gas; the raw materials are easy to obtain, the risk is low; 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...

Examples

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 ...

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...

Examples

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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