Sodium Hydroxide → 4-Chloro-2-fluoroaniline

Temperature

80 °C

Under a nitrogen atmosphere, a suspension of 718 g (3.8 moles) of 4-chloro-2-fluoroacetanilide in 2653 mL of ethanol was stirred as a solution of 304 g (7.6 moles) of sodium hydroxide in 1075 mL of water was added. Upon completion of addition the reaction mixture was warmed to 80° C. during a 2.3 hour period. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure to a volume of approximately 2000 mL. The concentrate was dissolved in 2000 mL of ethyl acetate and washed with 500 mL of water. The organic layer was concentrated under reduced pressure to a residual oil. The oil was filtered to remove a solid, then distilled under reduced pressure to yield 329 g of 4-chloro-2-fluoroaniline; b.p. 93°-100° C./16-20 mm.

1. additionwas added
2. additionUpon completion of addition the reaction mixture
3. temperatureThe reaction mixture was cooled to ambient temperature
4. concentrationconcentrated under reduced pressure to a volume of approximately 2000 mL
5. dissolutionThe concentrate was dissolved in 2000 mL of ethyl acetate
6. washwashed with 500 mL of water
7. concentrationThe organic layer was concentrated under reduced pressure to a residual oil
8. filtrationThe oil was filtered
9. customto remove a solid
10. distillationdistilled under reduced pressure

ORD record

ord-6c87480cd22d47b289582f2aa51ac600

Source dataset

uspto-grants-1990_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04906287