Ethanol → 3-Bromo-4-fluoroaniline

2-Bromo-1-fluoro-4-nitrobenzene was dissolved in tetrahydrofuran (75 ml) and ethanol (75 ml) and tin(II) chloride dihydrate added and the mixture left to stir at ambient temperature for 4 h. The solvent was evaporated and the residue was treated with ice-cold 2 N sodium hydroxide solution (200 ml). The resulting slurry was stirred for 30 min then extracted with dichloromethane (3×200 ml). The combined organic phase was washed with water (200 ml) and brine (200 ml), dried over anhydrous magnesium sulfate, filtered and evaporated to give 3-bromo-4-fluorophenylamine (7.92 g, 92%) as a yellow oil: 1H NMR (360 MHz, CDCl3) δ 3.53 (2H, s), 6.53-6.57 (1H, m), 6.83-6.85 (1H, m), 6.90 (1H, dd, J 9, 9 Hz).

1. waitthe mixture left
2. customThe solvent was evaporated
3. additionthe residue was treated with ice-cold 2 N sodium hydroxide solution (200 ml)
4. stirringThe resulting slurry was stirred for 30 min
5. extractionthen extracted with dichloromethane (3×200 ml)
6. washThe combined organic phase was washed with water (200 ml) and brine (200 ml)
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customevaporated

ORD record

ord-f832e97485d442afbebcc0ad6496c6ec

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06936608B2