Potassium Iodide → 1-Chloro-2-fluoro-5-iodo-3-(trifluoromethyl)benzene

In 300 mL of 6N hydrochloric acid, 4.00 g of 3-chloro-4-fluoro-5-trifluoromethylaniline was added, and stirred at room temperature for 30 minutes. In the mixture, a solution of 1.42 g of sodium nitrite in 5 mL of water was added dropwise at such a rate that internal temperature would not exceed 5° C. After the completion of the addition dropwise, it was continued to stir at the same temperature further for 1 hour. In the reaction mixture, a solution of 4.70 g of potassium iodide in 15 mL of water was added dropwise at the same temperature with stirring. After the completion of the addition dropwise, it was continued to stir at the same temperature further for 1 hour and then at room temperature for 15 hours. After the completion of the reaction, the reaction mixture was extracted with 50 mL of diethyl ether twice. The combined organic phases were dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.70 g of the crude aimed product as yellow oily substance. The resulting product was used as such without purification for the next step.

1. customexceed 5° C
2. additionAfter the completion of the addition dropwise
3. stirringto stir at the same temperature further for 1 hour
4. stirringwith stirring
5. additionAfter the completion of the addition dropwise
6. stirringto stir at the same temperature further for 1 hour
7. waitat room temperature for 15 hours
8. customAfter the completion of the reaction
9. extractionthe reaction mixture was extracted with 50 mL of diethyl ether twice
10. dry with materialdried over saturated sodium chloride aqueous solution
11. distillationanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure

ORD record

ord-91182be111ed493ab10242bf8df4c8c8

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987464B2