Stannous Chloride → 3-Bromo-2-fluoroaniline

Temperature

70 °C

2.0 g (9.09 mmol) of 3-bromo-2-fluoronitrobenzene were dissolved in 10 ml of dioxane, and 8.62 g (45.45 mmol) of tin(II) chloride were added at RT. After addition of a few drops of 1 N hydrochloric acid, the mixture was heated at 70° C. for 2 h. After cooling, the reaction mixture was concentrated under reduced pressure and the residue was taken up in ethyl acetate. The solution was washed successively twice with 1N aqueous sodium hydroxide solution, water and saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 997 mg (57.7% of theory) of the target compound.

1. temperatureAfter cooling
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. washThe solution was washed successively twice with 1N aqueous sodium hydroxide solution, water and saturated sodium chloride solution
4. dry with materialdried over magnesium sulphate
5. concentrationconcentrated under reduced pressure
6. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

ORD record

ord-84bfa53893044bdd9c81bddbd58c308a

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018414B2