Reaction Steps
Cu(I) iodide (10 mg, 0.05 mmol), potassium carbonate (276 mg, 2.0 mmol) and Methyl 3-iodobenzoate (276 mg, 1.0 mmol) were charged into a screw-capped test tube with Teflon-lining. The tube was evacuated and backfilled with argon (3 cycles). Anhydrous DME (1.0 mL) and 3-methoxythiophenol (124 μL, 1.0 mmol) were added by syringes at room temperature. The tube was heated to 80° C. and stirred for 22 hours. The reaction mixture was then allowed to reach room temperature. Ethyl acetate (approx. 5 mL) and dodecane (227 μL, GC standard) were added. The aliquot was analyzed GC. The reaction mixture was then filtered and concentrated. The crude product was purified by column chromatography on silica gel using hexane/ethyl acetate=20/1 to afford colorless liquid as the titled product (220 mg, 81% yield). Rf=0.5 (hexane/ethyl acetate=10/1). 1H NMR (CDCl3, 300 MHz) δ 8.02-8.03 (m, 1 H), 7.89 (dt, 1 H, J=1.2 Hz, 8.1 Hz), 7.45-7.49 (m, 1 H), 7.34 (t, 1 H, J=7.5 Hz), 7.21 (t, 1 H, J=8.1 Hz), 6.86-6.92 (m, 2 H), 6.79 (ddd, 1 H, J=0.6 Hz, 2.4 Hz, 8.1 Hz), 4.34 (q, 2 H, J=7.2 Hz), 3.76 (s, 3 H), 1.37 (t, 3 H, J=7.2 Hz). 13C NMR (CDCl3, 75 MHz) δ 166.0, 160.2, 136.5, 136.3, 135.2, 132.0, 131.7, 130.3, 129.3, 128.4, 123.7, 116.6, 113.5, 61.5, 55.7, 14.7. IR (neat, cm−1) 3064, 2981, 2960, 2937, 2360, 2342, 1717. MS (EI) m/z (relative intensity) 288 (100), 243 (30). Anal. Cald. for C16H16O3S, Cald. C: 66.64, H: 5.59; Found C: 66.87, H: 5.66.
