p-Fluoronitrobenzene → Benzenamine, 3-(4-nitrophenoxy)-

Temperature

80 °C

To a solution of 1-fluoro-4-nitrobenzene (14.1 g, 100 mmol) and 3-aminophenol (11.2 g, 102 mmol) in N,N-dimethylformamide (150 mL) was added potassium carbonate (26.5 g, 191 mmol) and the mixture was stirred at 80° C. for 8 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate-hexane (1:1, 250 mL) and washed with water (250 mL×2) and saturated brine (100 mL), successively. The collected aqueous layer was extracted with ethyl acetate-hexane (1:1, 250 mL). The collected organic layer was dried over anhydrous magnesium sulfate, and decolorized with activated carbon. The insoluble material was filtered off through a pad filled with two layers of silica gel and celite, and the filtrate was concentrated. The obtained yellow syrup-like substance was recrystallized from ethyl acetate and hexane to give the title compound (21.8 g, 95%) as yellow crystals.

1. temperatureThe reaction mixture was cooled to room temperature
2. washwashed with water (250 mL×2) and saturated brine (100 mL)
3. extractionThe collected aqueous layer was extracted with ethyl acetate-hexane (1:1, 250 mL)
4. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
5. filtrationThe insoluble material was filtered off through a pad
6. additionfilled with two layers of silica gel and celite
7. concentrationthe filtrate was concentrated
8. customThe obtained yellow syrup-like substance was recrystallized from ethyl acetate and hexane

ORD record

ord-cdb5550ad8cc4ec0ae738d57618b64f3

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324395B2