Water → 4-Methyl-2-phenylaniline

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 2-bromo-4-methylbenzenamine (0.301 g, 1.618 mmol), phenyl boronic acid (0.296 g, 2.427 mmol), and tetrakistriphenylphosphine palladium(0) (0.187 g, 0.162 mmol) in DME (8 mL) was added 2M sodium carbonate solution (3 ml, 6 mmol) and the mixture was stirred for 16 h at 80° C. Water (30 ml) was added and the product was extracted with EtOAc (2×30 mL). The combined organics were washed with brine, dried (Na2SO4), concentrated and purified by silica gel chromatography to provide 2-phenyl-4-methylbenzenamine as a thick syrup (0.22 g, 75% yield). 1H NMR (400 MHz, CDCl3): δ 7.47-7.41 (m, 4H), 7.36-7.32 (m, 1H), 6.99-6.96 (m, 2H), 6.71 (d, J=8.0 Hz, 1H), 2.28 (s, 3H); MS (ESI) m/z: 184.2 (M+H+).

Provenance & Evidence