Ethyl bromoacetate → Ethyl 2-(5-fluoro-2-nitrophenoxy)acetate

To a mixture consisting of 5-fluoro-2-nitrophenol (47.1 g), acetonitrile (300 ml) and potassium carbonate (46 g) was added ethyl bromoacetate (60.1 g) dropwise at a temperature from 50° to 60° C., followed by a five-hour refluxing under heating and then filtration under cooling. The resulting filtrate was subjected to distillation under reduced pressure, and then dissolved in toluene (350 ml). The resulting toluene solution was washed with water, a 5% aqueous solution of potassium hydroxide, and water, in that order, followed by drying with magnesium sulfate and the toluene was distilled off therefrom under reduced pressure. The residue was distilled under reduced pressure to collect a fraction boiling at from 154° to 156° C., so as to obtain ethyl 5-fluoro-2-nitrophenoxyacetate (65.3 g). The whole quantity of the reaction product was dissolved in ethanol (8.1 l), followed by addition thereto of a solution of ammonium chloride (60 g) and water (400 ml). To the resulting mixture was added zinc dust (60.5 g) portionwise at a temperature of from 20° to 30° C.

1. waitfollowed by a five-hour
2. temperaturerefluxing
3. temperatureunder heating
4. filtrationfiltration
5. temperatureunder cooling
6. distillationThe resulting filtrate was subjected to distillation under reduced pressure
7. dissolutiondissolved in toluene (350 ml)
8. washThe resulting toluene solution was washed with water
9. dry with materialby drying with magnesium sulfate
10. distillationthe toluene was distilled off
11. distillationThe residue was distilled under reduced pressure
12. customto collect a fraction
13. customboiling at from 154° to 156° C.

ORD record

ord-dc388e3085664314a2d3ace37e34c634

Source dataset

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05207818