Dibutyl sulfide → Butyl p-tolyl sulfide

Participants

Reaction Steps

The general procedure was used to convert 4-iodotoluene and n-butyl sulfide to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a clear oil (331 mg, 94% yield). 1H NMR (300 MHz, CDCl3) δ 7.15–7.12 (d, J=8.2, 2H; Ha, Ha′), 6.98–6.96 (d, J=7.9, 2H; Hb, Hb′), 2.79–2.74 (t, J=7.1, 2H; Hc), 2.20 (Methyl Protons), 1.55–1.45 (m, 2H; Hd), 1.39–1.15 (m, 2H; He), 0.83–0.78 (t, J=7.1, 3H; Hf). 13C NMR (75 MHz, CDCl3) δ 135.6 (C4), 133 (C3), 129.6 (C1, C1′), 129.47 (C2, C2), 33.8 (methyl protons), 31.2 (C5), 21.8 (C6), 20.8 (C7), 13.54 (C8). Anal. Calcd. for C11H16S: C, 73.27; H, 8.94; S, 17.78; Found C, 73.21; H, 9.15; S, 17.57.

Provenance & Evidence