Water → 5-Bromo-2-(trifluoromethyl)aniline

Temperature

80 °C

To a suspension of 4-bromo-2-nitro-1-(trifluoromethyl)benzene (4.0 g, 14.9 mmol) in ethanol (230 mL), THF (85 mL), and water (40 mL) was added ammonium chloride (1.0 g, 18.8 mmol) and ferrous powder (5.06 g, 90 mmol). The resulting mixture was heated at 80° C. for 1 hr and the progress of the reaction was monitored by TLC. Upon complete consumption of staring material, the reaction mixture was filtered off while it was hot. The filtrate was evaporated under vacuum and the crude residue was diluted with ethyl acetate (100 mL) and washed with water (3×50 mL). The combined organic layer was washed with brine, dried over Na2SO4 and evaporated under vacuum to afford 5-bromo-2-(trifluoromethyl)aniline as a solid (3.2 g, 90%).

1. customUpon complete consumption of staring material
2. filtrationthe reaction mixture was filtered off while it
3. customThe filtrate was evaporated under vacuum
4. additionthe crude residue was diluted with ethyl acetate (100 mL)
5. washwashed with water (3×50 mL)
6. washThe combined organic layer was washed with brine
7. dry with materialdried over Na2SO4
8. customevaporated under vacuum

ORD record

ord-d885e98df8414def9d1a4e7ebedcdc74

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073891B2