Acetic Anhydride → N-(3-Chloro-4-fluorophenyl)-N-ethylacetamide

A solution of 3-chloro-N-ethyl-4-fluoroaniline (97.4 g, 0.56 mmol) in glacial acetic acid (225 ml) is treated at 5° with acetic anhydride (105 ml, 1.12 mol). The solution is stirred for one hour, then poured on to ice/water (250 ml) and extracted with ethyl acetate (2×200 ml). The combined phases are washed in succession with water (100 ml), 2N sodium hydroxide solution (100 ml), saturated sodium bicarbonate solution (100 ml), water (10 ml) and 10 percent sodium chloride solution (100 ml). The solution is dried over magnesium sulfate and evaporated. The residue is recrystallized from n-hexane. There are obtained 102 g (84.2%) of 3'-chloro-N-ethyl-4'-fluoroacetanilide.

1. extractionextracted with ethyl acetate (2×200 ml)
2. washThe combined phases are washed in succession with water (100 ml), 2N sodium hydroxide solution (100 ml), saturated sodium bicarbonate solution (100 ml), water (10 ml) and 10 percent sodium chloride solution (100 ml)
3. dry with materialThe solution is dried over magnesium sulfate
4. customevaporated
5. customThe residue is recrystallized from n-hexane

ORD record

ord-67abc515b07741f3a00401010659d950

Source dataset

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05283248