Water → 4-Bromo-2-fluoro-5-methoxyaniline

To a stirred solution of 30.0 g (0.12 mole) of 4-bromo-2-fluoro-5-methoxynitrobenzene in 200 mL of acetic acid was added 40 mL of water, followed by the portionwise addition of 30.0 g (0.54 mole) of iron filings during a 2.5 hour period. Upon complete addition, the reaction mixture was stirred at 25°-35° C. for one hour. Diethyl ether, 200 mL, was added, and the reaction mixture was filtered through a pad of diatomaceous earth. The filtrate was washed with 200 mL of water. The organic layer was separated and neutralized with solid sodium bicarbonate. The mixture was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a residual solid. The solid was recrystallized from petroleum ether to give 23.5 g of 4-bromo-2-fluoro-5-methoxyaniline; m.p. 60°-62° C.

1. additionUpon complete addition
2. filtrationthe reaction mixture was filtered through a pad of diatomaceous earth
3. washThe filtrate was washed with 200 mL of water
4. customThe organic layer was separated
5. dry with materialThe mixture was dried with magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure
8. customto give a residual solid
9. customThe solid was recrystallized from petroleum ether

ORD record

ord-b8c8a65775c340c5a0c90065b97d6c4b

Source dataset

uspto-grants-1989_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04818276