2-Bromo-5-nitrophenol → 5-Amino-2-trifluoromethyl-phenol

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Reaction Steps

To a solution of 5-nitro-2-(trifluoromethyl)phenol and 2-bromo-5-nitrophenol (10 g, crude) in MeOH (60 mL) was added Raney Ni (2 g) under an atmosphere of nitrogen. The mixture was stirred under hydrogen atmosphere (1 atm) at r. t. for 4 h. The catalyst was filtered off through the celite pad and the filtrate was evaporated under vacuum. The crude product was purified by preparative HPLC to obtain 5-amino-2-(trifluoromethyl)phenol (1.7 g, 11% yield for 3 steps). 1H-NMR (400 MHz, DMSO-d6) δ 9.79 (s, 1 H), 7.04 (d, J=8.8 Hz, 1 H), 6.10 (s, 1 H), 6.01 (d, J=8.4 Hz, 1 H), 5.58 (br s, 2 H).

Provenance & Evidence