4-Fluoro-2-nitro-1-phenoxybenzene → 5-Fluoro-2-phenoxyaniline

Temperature

25 °C

The atmosphere over a stirred solution of 11,6 g (50 mmol) 4-fluoro-2-nitro-1-phenoxy-benzene and catalytic amount of palladium on carbon in 150 ml iso-propanol at 20° C. was saturated with hydrogen. The reaction mixture was stirred vigorously at 25° C. for 8 h. The reaction mixture was filtered over celite. The filtrate was evaporated. 200 ml water and 200 ml dichloromethane were added. The organic phase was separated. The aqueous phase was extracted three times with 100 ml dichloromethane each. The combined organic phases were washed with 50 ml water and 50 ml brine. The organic phase was dried with magnesium sulfate and evaporated. The crude product 1b was used without purification. The desired crude product 1b was obtained in 94% yield (9.54 g, 47 mmol) as yellow oil.

1. customat 20° C.
2. filtrationThe reaction mixture was filtered over celite
3. customThe filtrate was evaporated
4. addition200 ml water and 200 ml dichloromethane were added
5. customThe organic phase was separated
6. extractionThe aqueous phase was extracted three times with 100 ml dichloromethane each
7. washThe combined organic phases were washed with 50 ml water and 50 ml brine
8. dry with materialThe organic phase was dried with magnesium sulfate
9. customevaporated
10. customThe crude product 1b was used without purification

ORD record

ord-d1310dc3efba4c02b93d2fb7e395b7ac

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803960B2