Sodium Hydroxide → 4-[(1,3-Difluoropropan-2-yl)oxy]aniline

3.4 g (15.7 mmol) of p-(1,3-difluoro-2-propoxy)nitrobenzene, 17.7 g (78.5 mmol) of SnCl2 ·2H2O and 35 ml of absolute ethanol were heated together at reflux for 1 hour. The reaction mixture was poured over ice, made basic with 50 percent aqueous NaOH and extracted three times into ether. The combined ether extracts were washed two times with water, dried over MgSO4 and filtered. Hydrogen chloride gas was bubbled into the ether solution causing the above-named aniline to precipitate as the hydrochloride salt. The product was collected as a tan solid by filtration (80 percent of theoretical) and decomposed (d) at 240° C. T1 - % C? % H? % N? -Analysis: -Calc. for C9H11F2NO.HCl: 48.33 5.41 6.26 -Found: 48.42 5.41 6.33 -

1. temperatureat reflux for 1 hour
2. additionThe reaction mixture was poured over ice
3. extractionextracted three times into ether
4. washThe combined ether extracts were washed two times with water
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customHydrogen chloride gas was bubbled into the ether solution
8. customto precipitate as the hydrochloride salt
9. filtrationThe product was collected as a tan solid by filtration (80 percent of theoretical)
10. customat 240° C

ORD record

ord-9acd510732364543bec6f0b75bb73a0f

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05250690