Acetic Acid → 2-Bromo-1-fluoro-4-nitrobenzene

Temperature

0 °C

To a mixture of 2-fluoro-5-nitroaniline (25.90 g), 47% aqueous hydrogen bromide (100 ml), water (200 ml) and acetic acid (200 ml) was added dropwise an aqueous sodium nitrite (11.56 g) solution (100 ml), and the mixture was stirred at 0° C. for 1 h. This mixture was added at 0° C. to a solution of copper bromide (CuBr: 27.30 g) dissolved in 47% aqueous hydrogen bromide (100 ml) and the mixture was stirred at room temperature for 16 h. The reaction mixture was extracted with ethyl acetate, dried (anhydrous magnesium sulfate) and concentrated under reduced pressure. The residue was purified by silica gel chomatography (eluent: hexane). Crystallization from hexane gave the title compound (4.01 g) as colorless needle crystals.

1. stirringthe mixture was stirred at room temperature for 16 h
2. extractionThe reaction mixture was extracted with ethyl acetate
3. dry with materialdried (anhydrous magnesium sulfate)
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by silica gel chomatography (eluent: hexane)
6. customCrystallization from hexane

ORD record

ord-9a72eb79c87944d7a3fa39320c153883

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06518257B1