4-Aminophenol → 4-(2-Chloro-1,1-difluoroethoxy)benzeneamine

2.5 g (22.9 mmol) of p-aminophenol, 3.09 g (22.9 mmol) of 1,2-dichloro-1,1-difluoroethane, 5.48 g (39.6 mmol) of K2CO3 and 40 ml of dry acetonitrile were stirred together at room temperature for 5 days. The mixture was poured into water and extracted two times into ether. The combined ether extracts were washed with water, dried over MgSO4 and filtered: HCl gas was bubbled into the ether solution causing the above-named aniline to precipitate as the hydrochloride salt, which was collected by filtration and recrystallized twice from CH3CN to give 0.9 g (16 percent of theoretical d 245°-250° C.) of a white solid.

1. extractionextracted two times into ether
2. washThe combined ether extracts were washed with water
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customHCl gas was bubbled into the ether solution
6. customto precipitate as the hydrochloride salt, which
7. filtrationwas collected by filtration
8. customrecrystallized twice from CH3CN
9. customto give 0.9 g (16 percent of theoretical d 245°-250° C.) of a white solid

ORD record

ord-c511a8c8feb8478d9e51ff3b4f62f5c5

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05250690