p-Fluoronitrobenzene → HCID 71015326, compound

Temperature

0 °C

Into a 500 mL 3-necked round-bottom flask, was placed a solution of sodium hydride (3.9 g, 162.50 mmol, 1.7 equiv) in N,N-dimethylformamide (200 mL). This was followed by the addition of a solution of 1-fluoro-4-nitrobenzene (13.6 g, 96.39 mmol, 1.00 equiv) in N,N-dimethylformamide (50 mL) dropwise with stirring at 0° C. over 20 min. The reaction mixture was stirred for 2 hr at 25° C. and then CuCl (9.6 g, 96.97 mmol, 1.0 equiv) was added, followed by addition of a solution of 2,5-difluorophenol (15.5 g, 119.15 mmol, 1.2 equiv) in N,N-dimethylformamide (50 mL) dropwise with stirring at 25° C. over 10 min. The resulting solution was stirred for 12 h at 100° C. in an oil bath and then diluted with water and washed with ether, water and brine. The reaction mixture was dried over anhydrous sodium sulfate and concentrated. The residue was loaded onto a silica gel column and eluted with ethyl acetate/petroleum ether (1/8) to give 19.5 g (81%) of 1,4-difluoro-2-(4-nitrophenoxy)benzene as a brown solid,

1. customInto a 500 mL 3-necked round-bottom flask, was placed
2. stirringThe reaction mixture was stirred for 2 hr at 25° C.
3. stirringwith stirring at 25° C. over 10 min
4. stirringThe resulting solution was stirred for 12 h at 100° C. in an oil bath
5. washwashed with ether, water and brine
6. dry with materialThe reaction mixture was dried over anhydrous sodium sulfate
7. concentrationconcentrated
8. washeluted with ethyl acetate/petroleum ether (1/8)

ORD record

ord-8c7c925249f0495c9e7dc0f5a861f1e5

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946241B2