p-Fluoronitrobenzene → HCID 71015356, compound

Temperature

0 °C

Into a 500 mL, 4-necked round-bottom flask purged and maintained under an inert atmosphere of nitrogen, was placed a solution of sodium hydride (6.8 g, 170.00 mmol, 1.70 equiv, 60%) in N,N-dimethylformamide (200 mL). A solution of 1-fluoro-4-nitrobenzene (14.1 g, 99.93 mmol, 1.00 equiv) in N,N-dimethylformamide (50 mL) was added dropwise with stirring at 0° C. in 15 min. The resulting solution was stirred for 2 h at room temperature. CuCl (10 g, 101.01 mmol, 1.00 equiv) was added and a solution of 2,3-difluorophenol (15.6 g, 119.91 mmol, 1.20 equiv) in N,N-dimethylformamide (50 mL) was added dropwise with stirring. The resulting solution was allowed to react, with stirring, for an additional 12 h while the temperature was maintained at 100° C., in an oil bath. The resulting solution was extracted with ether and the organic layers combined. The organic layers was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was loaded onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:8) to give 21.2 g (84%) of 1,2-difluoro-3-(4-nitrophenoxy)benzene as a brown solid.

1. customInto a 500 mL, 4-necked round-bottom flask purged
2. temperaturemaintained under an inert atmosphere of nitrogen
3. stirringThe resulting solution was stirred for 2 h at room temperature
4. stirringwith stirring
5. customto react
6. stirringwith stirring, for an additional 12 h while the temperature
7. temperaturewas maintained at 100° C., in an oil bath
8. extractionThe resulting solution was extracted with ether
9. washThe organic layers was washed with water and brine
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated under vacuum
12. washeluted with ethyl acetate/petroleum ether (1:8)

ORD record

ord-54b7e317111c430fb79e09ab6ca750d2

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962831B2