Toluene → HCID 86607748, compound

Participants

Reaction Conditions

Reaction Steps

2.04 g (10.0 mmol) of 3-bromothioanisole (1), 1.65 g (11.0 mmol) of 4-butylaniline (2), 23 mg (0.025 mmol) of Pd2(dba)3, 42 mg (0.075 mmol) of 1,1′-bis(diphenylphosphino) ferrocene (“DPPF”) and 1.34 g (14 mmol) of t-BuONa were dissolved in 20 mL of toluene. The mixture was stirred for 24 h at 90° C. After cooling to room temperature, it was diluted with 150 mL of diethyl ether and filtered. The solvent was evaporated and the residue was purified by liquid chromatography on silica gel (chloroform/hexane=1:1) to give 2.05 g of N-4-butylphenyl-N-3-methylthiophenylamine (3) (75%). 1H-NMR (400 MHz, CDCl3): δ 7.19 (t, 8 Hz, 1H), 7.15 (m, 2 H), 7.06 (m, 2H), 6.96 (t, J=2 Hz, 1 H), 6.83 (m, 1 H), 6.813 (m, 1H), 2.63 (t, J=7.6 Hz, 2H), 2.49 (s, 3 H), 1.65(m, 2 H), 1.43 (tq, J1,J2=7.2 Hz, 2H), 1.00 (t, J=7.2 Hz, 3H). GC-MS: m/z=273 (M+).

Provenance & Evidence