Yield: 90%

Reaction Conditions:

with iron;ammonium chloride in tetrahydrofuran;ethanol;water at 80; for 1 h;

Steps:

To a suspension of 4-bromo-2-nitro- 1 -(trifluoromethyl)benzene (4.0 g, 14.9mmol) in ethanol (23OmL), THF (85mL), and water (4OmL) was added ammonium chloride (1.0 g, 18.8mmol) and ferrous powder (5.06 g, 90mmol). The resulting mixture was heated at 80 ⁰C 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 (10OmL) and washed with water (3 x 5OmL). 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 (3.2g, 90%).

References:

ELAN PHARMACEUTICALS, INC.;SHAM, Hing, L.;KONRADI, Andrei, W.;HOM, Roy, K.;PROBST, Gary, D.;BOWERS, Simeon;TRUONG, Anh;NEITZ, R., Jeffrey;SEALY, Jennifer;TOTH, Gergely WO2010/91310, 2010, A1 Location in patent:Page/Page column 100