Nitrogen → HCID 86750104, compound

Participants

Reaction Steps

To a stirred solution of 1,4-diiodobenzene (9.9 g, 30 mmol) in anhydrous tetrahydrofuran (100 ml) was added n-butyllithium (18.75 ml, 1.6M in hexanes, 30 mmol) dropwise under N2 at -78° C., and stirring was continued for 15 min. A solution of 1-(4-(8-chlorooctoxy-phenyl)-2-phenyl-1-butanone (11.18 g, 29 mmol) in tetrahydrofuran (50 ml) was added and stirring continued at -78° C. for 2 h. Then the mixture was allowed to warm to room temperature. After 16 h, the mixture was quenched with saturated ammonium chloride solution (10 ml), poured into ether (100 ml) and washed with brine (50 ml) and water (2×50 ml). The organic layer was dried (MgSO4), and concentrated in vacuo. The residues were dissolved in ethanol (100 ml), concentrated hydrochloric acid (50 ml) was added and the mixture was refluxed for 4 h. The ethanol was removed in vacuo, the residues were dissolved in ether (50 ml), washed with water (3×50 ml), dried (MgSO4) and concentrated in vacuo. The residues were column-chromatographed (silica; eluant: 10% dichloromethane in petrol) to give a mixture of the title compound and the Z Isomer as a viscous colourless oil (13.6 g). Crystalisation from ethanol gave the title compound as white crystals (5.35 g, 31%) mp 64°-66° C. NMR (CDCl3) δ=0.89 (3H,t,J=7.5 Hz), 1.26-1.46 (8H, m), 1.60-1.80 (4H,m), 2.415 (2H,q,J=7.4 Hz), 3.50 (2H,t,J=6.6 Hz), 3.79 (2H,t,J=6.6 Hz), 6.505 (2H,d,J=8.7 Hz), 6.705 (2H,d,J=8.7 Hz), 6.965 (2H,d,J=8.4 Hz), 7.07-7.19 (5H,m), 7.65 (2H,d,J=8.2 Hz). IR (evap, cm-1) 2931, 2857, 1606, 1509. MS(CI) m/e=574 (M+ +1, 10%) Analysis C30H34ClIO requires C 62.89, H 5.98, Cl 6.19, I 22.15; found C 66.92, H 5.95, Cl 6.30, I 22.05%

Provenance & Evidence