Heptadecylamine → HCID 67247093, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,3-dibromo-2,2′-bithiophene (4.92 g, 15.3 mmol), t-BuONa (3.54 g, 36.8 mmol), Pd2 dba3 (0.35 g, 0.382 mmol) and BINAP (0.95 g, 1.53 mmol) in toluene (38 mL) under an argon atmosphere was added 9-octylnonylamine (4 g, 15.7 mmol). The reaction mixture was subsequently stirred at 110° C. over a period of 7 hours. The reaction mixture was allowed to cool to room temperature followed by the addition of water. The organic layer was removed and the remaining aqueous phase extracted several times with diethyl ether. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. Purification by column chromatography using hexanes as the eluant afforded the title compound as a light green solid (5.2 g, 81% yield): mp: 60° C.; GC-Ms: 417.5; 1H NMR (400 MHz, CDCl3, ppm) δ: 7.11(d, 2H), 7.02-7.01(d, 2H), 4.23-4.19(m, 1H), 2.08(m, 2H), 1.85-1.80(m, 2H), 1.22-1.07(m, 24 H), 0.86-0.82(t, 6 H); 13C NMR (100 MHz, CDCl3, ppm) δ: 144.2, 122, 4, 114.9, 59.9, 35.4, 31.9, 29.4, 29.3, 26.7, 22.8, 14.2.

Provenance & Evidence