Sodium Carbonate → 2-Methyl-4'-(trifluoromethyl)biphenyl-3-amine

Participants

Reaction Steps

To a solution of 3-bromo-2-methylaniline (1.19 g, 6.4 mmol) in DME (30 mL) and water (15 mL) was added para-trifluoromethylphenyl boronic acid (1.82 g, 9.6 mmol) and sodium carbonate (1.76 g, 16.6 mmol). The apparatus was flushed with nitrogen prior to the addition of tetrakis (triphenylphosphine) palladium (0) (0.22 g, 0.19 mmol). The resultant mixture was heated to reflux and stirred under nitrogen for 17 h, then allowed to cool to room temperature and the solvents removed in vacuo. The residue was partitioned between EtOAc (2×60 mL) and water (60 mL). The organic solution was dried (MgSO4) and the solvent was removed in vacuo. Purification by Biotage™ chromatography (90 g Silica column) eluted with 1:4 EtOAc:cyclohexane afforded the title compound as a cream coloured solid (1.27 g).

Provenance & Evidence