Sulfuryl chloride → 4-Chloro-2,6-Difluoroaniline

Temperature

80 °C

35.5 g of 2,6-difluoroaniline were mixed with 200 ml of concentrated acetic acid, and the mixture was heated to 80° C. 42.4 g of sulfuryl chloride were mixed with approximately the same amount of concentrated acetic acid, and the mixture was added dropwise to the heated solution. The mixture was then heated at reflux for six hours. After cooling, the solution was concentrated under reduced pressure and the residue was stirred with water and pentane. The solid residue was filtered off and washed with water. The resulting solid was admixed with 200 ml of concentrated hydrochloric acid and heated at reflux for two hours. After cooling, the solution was carefully made slightly alkaline using aqueous sodium hydroxide solution, and the mixture was extracted three times with 100 ml of ethyl acetate each time. The organic phase was dried over sodium sulfate and freed from the solvent. Yield: 40 g;

1. additionthe mixture was added dropwise to the heated solution
2. temperatureThe mixture was then heated
3. temperatureat reflux for six hours
4. temperatureAfter cooling
5. concentrationthe solution was concentrated under reduced pressure
6. filtrationThe solid residue was filtered off
7. washwashed with water
8. temperatureheated
9. temperatureat reflux for two hours
10. temperatureAfter cooling
11. extractionthe mixture was extracted three times with 100 ml of ethyl acetate each time
12. dry with materialThe organic phase was dried over sodium sulfate

ORD record

ord-8be5f2eff7ee467e83a9d27e4bd07ca0

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06624119B1