Benzene → 3-(3-Hydroxyprop-1-ynyl)-N-phenylbenzenesulfonamide

Participants

Reaction Steps

A mixture of 3-bromo-N-phenyl-benzenesulfonamide (52a) (1.0 g, 3.2 mmol), benzene (2.4 ml), tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.34 mmol), copper iodide (0.032 g, 0.16 mmol), triethylamine (2.4 ml, 17.2 mmol), and propargyl alcohol (1.0 ml, 17.2 mmol)) was refluxed under argon for 30 min. The reaction mixture was diluted with 5% HCl (50 ml) and product was extracted with ethyl acetate (50 ml). The extract was washed successively with 5% NaHCO3, water and dried (Na2SO4). The solvents were removed under reduced pressure and the product was purified on silica gel with ethyl acetate-hexane (1:1, v/v) as eluent. The title compound (0.59 g, 64%) was obtained as an oil. 1H NMR (DMSO-d6, HMDSO) δ: 4.29 (2H, d, J=6.0 Hz, CH2); 5.36 (1H, t, J=6.0 Hz, OH); 6.94–7.32 (5H, m, C6H5); 7.35–7.91 (4H, m, C6H4); 10.32 (1H, s, NH).

Provenance & Evidence