Acetic Acid → 2-((2-Methoxy-4-(trifluoromethyl)phenyl)amino)-5-nitrophenol

Participants

Reaction Conditions

Reaction Steps

Dissolved 2-amino-5-nitrophenol (4.0 g, 26.0 mmol), cesium carbonate (23.25 g, 71.4 mmol), and copper(i) iodide (4.94 g, 26.0 mmol) in DMF (43.3 ml) in a 250 mL sealed tube and stirred at 25° C. for 30 min. Then added 1-bromo-2-methoxy-4-(trifluoromethyl)benzene (5.52 g, 21.63 mmol) and stirred for 18 h at 100° C. Added acetic acid (8.67 ml, 151 mmol) to neutralize base and product. Diluted the reaction with a solution of DCM/MeOH/NH4OH (90:10:1) and filtered through a frit of silica to remove some of the copper and base, rinsing with more of the solution. The collected eluent was concentrated, then purified using silica gel chromatography using a gradient of (0-100%) Hex:EtOAc to yield 2-((2-methoxy-4-(trifluoromethyl)phenyl)amino)-5-nitrophenol (1.75 g, 5.33 mmol, 24.65% yield) as a yellow solid.

Provenance & Evidence