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ChemicalBook CAS DataBase List 2-Bromo-4-fluorobenzaldehyde
59142-68-6

2-Bromo-4-fluorobenzaldehyde synthesis

7synthesis methods
2-BROMO-4-FLUOROBENZYL ALCOHOL

229027-89-8

2-Bromo-4-fluorobenzaldehyde

59142-68-6

The general procedure for the synthesis of 2-bromo-4-fluorobenzaldehyde from 2-bromo-4-fluorobenzyl alcohol was as follows: benzyl alcohol substrate (0.2 mmol), FeCl3-6H2O (0.002 mmol, 5.4 mg) and triphenylmethanol (0.2 mmol, 52 mg) were mixed in a dry reaction vessel. Subsequently, the reaction mixture was irradiated in a microwave reactor at 55 °C for 1 hour. Upon completion of the reaction, the crude product was purified by fast column chromatography to afford the target product 2-bromo-4-fluorobenzaldehyde.

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Yield:59142-68-6 85%

Reaction Conditions:

with sulfuric acid;5,5-dibromohydantoin;trifluoroacetic acid at 0 - 50; for 56 h;Autoclave;Large scale;Reagent/catalyst;

Steps:

1-3 Example 3
Add 50 liters of trifluoroacetic acid/H2SO4 mixed solvent (volume ratio 5/1) to a 100 liter autoclave equipped with a motorized stirrer, drop to 0 ° C, and then add 6.24 kg (25 mol) of 4-fluorobenzaldehyde then raise to 50 ° C under stirring, add 7.15 kg (25 mol) of dibromohydantoin solid from the feed port, seal the feed port after the addition, keep the reaction system at 50 ° C for 8 hours; open the feed port Further, 7.15 kg (50 mmol) of dibromohydantoin solid was added, and the mixture was stirred at 50 ° C for 48 hours. After the reaction of the raw materials was completed, the temperature was lowered to room temperature, and the reaction liquid was slowly poured into 500 liters of ice water, and the aqueous phase was extracted with n-hexane (50 L×3), the organic phase was combined, and the organic phase was washed once with 10 L of saturated sodium hydrogencarbonate solution, 10 L. The saturated sodium chloride solution was washed once, and the organic phase was concentrated under reduced pressure to remove n-hexane to obtain crude product of 2-bromo-4-fluorobenzaldehyde. The crude product was distilled under reduced pressure by an oil pump to obtain 8.63 kg of 2-bromo-4-fluorobenzaldehyde. The target product, the product is a colorless viscous liquid, the yield is 85%.

References:

Jiangsu Institute Of Technology;Luo Shipeng;Zhang Jinlong;Wang Xin;Yang Tinghai;Liu Weiqiao CN109809977, 2019, A Location in patent:Paragraph 0027; 0028; 0034; 0035; 0036; 0037

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