4-Fluoroaniline → Picolinafen

Temperature

150 °C

10.26 g (37.5 mmol) of 2-chloro-6-[3-(trifluoromethyl)phenoxy]pyridine (content: 99.5 percent, prepared according to Example 1), 6.25 g (56.2 mmol) of 4-fluoroaniline, 4.37 g (41.3 mmol) of sodium carbonate, 26.3 mg (37.5 μmol) of dichlorobis(triphenylphosphine)palladium(II) and 0.40 g (1.125 mmol) of tris(4-methoxyphenyl)phosphine (IV, R8 =R9 =R10 =methoxy) in 37.5 ml of xylene were placed in an autoclave at room temperature. The autoclave was flushed with inert gas, a carbon monoxide pressure of 5 bar was then applied and the mixture was heated to 150° C. The CO pressure was raised to 18 bar and the mixture was stirred for 21 hours at 150° C. After cooling to room temperature and depressurization, 50 ml of xylene and 50 ml of water were added to the reaction mixture, which was filtered. The aqueous phase was extracted with 25 ml of xylene and the combined organic phases were washed with 30 ml of water. Neither unconverted educt nor by-products were detectable by GC in the xylene phase. After distillation of the solvent, the crude product (15.83 g) was obtained in the form of a yellow solid. The crude product was purified by recrystallization from methylcyclohexane. The yield was 12.13 g (86 percent) of a light beige solid. Other data concerning the product was:

1. customwere placed in an autoclave at room temperature
2. customThe autoclave was flushed with inert gas
3. temperatureThe CO pressure was raised to 18 bar
4. temperatureAfter cooling to room temperature
5. additiondepressurization, 50 ml of xylene and 50 ml of water were added to the reaction mixture, which
6. filtrationwas filtered
7. extractionThe aqueous phase was extracted with 25 ml of xylene
8. washthe combined organic phases were washed with 30 ml of water
9. distillationAfter distillation of the solvent

ORD record

ord-decb05b7cc0e42668a8572e9773eed2e

Source dataset

uspto-grants-1999_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05892032