Toluene → 2-Methoxy-4-nitro-1-(trifluoromethyl)benzene

Temperature

155 °C

To a solution of 1-bromo-2-methoxy-4-nitrobenzene (10.0 g, 43.0 mmol) in N,N-dimethylformamide (200 mL) were added potassium trifluoroacetate (13.0 g, 86.0 mmol), copper iodide(I) and toluene (40 mL), and the mixture was stirred at 155° C. for 20 hr while removing the produced water drops by a Dean-Stark trap. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was suspended in ethyl acetate (300 mL), the insoluble material was filtered off, and the filtrate was washed with water (150 mL) and saturated brine (150 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=98/2→88/12). The obtained solution was concentrated under reduced pressure to give the title compound (6.86 g, 72%) as a pale-yellow oil.

1. customwhile removing the produced water drops by a Dean-Stark trap
2. temperatureThe reaction mixture was cooled to room temperature
3. concentrationconcentrated under reduced pressure
4. filtrationthe insoluble material was filtered off
5. washthe filtrate was washed with water (150 mL) and saturated brine (150 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationThe insoluble material was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=98/2→88/12)
10. concentrationThe obtained solution was concentrated under reduced pressure

ORD record

ord-0ead6b0775564abf935e2d2a1f432887

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2