4-Iodoaniline → HCID 15515315, compound

Participants

Reaction Conditions

Reaction Steps

4-Iodoaniline (10 g, 45 mmol), palladium on carbon (2.86 g, 1.35 mmol, 5% w/w), PPh3 (1.4 g, 5.4 mmol), CuI (513 mg, 2.7 mmol), and K2CO3 (15 g, 5.4 mmol) were added to DME (50 mL) and H2O (50 mL). The mixture is degassed while stirring by bubbling nitrogen vigorously into the solution. Pent-4-yn-1-ol (10.5 mL, 114 mmol) was added by syringe. The mixture was heated at 85° C. After cooling, water (100 mL) and EtOAc (200 mL) were added. The mixture was extracted with EtOAc. The organic layer and the water layer were independently neutralized with 1N HCl. The aqueous layer was extracted with EtOAc and the combined organic layers dried over MgSO4. The material was concentrated by rotary evaporation and the oil was purified by chromatography (gradient 10-100% EtOAc/Hex) to give the title compound as a dark oil (6 g, 76%). 1H NMR (400 MHz, CDCl3) δ 7.19 (dd, 2H, J=8.9, 1.5 Hz), 6.58 (dd, 2H, J=8.9, 1.5 Hz), 3.85 (t, 2H, J=8.0 Hz), 3.75 (brs, 2H), 2.55 (t, 2H, J=8.0 Hz), 1.86 (m, 2H); ES/MS calcd. for C11H14NO+ 176.1. Found m/z=176.1 (M+H)+.

Provenance & Evidence