4-Iodophenol → Ethyl 2-(4-((4-hydroxyphenyl)ethynyl)phenoxy)acetate

Participants

Reaction Steps

To a dried Schlenk flask filled with nitrogen was added Pd(PPh3)4 (56.5 mg, 0.049 mmol), CuI (14.2 mg, 0.075 mmol), ethyl 2-(4-ethynylphenoxy)acetate (150.0 mg, 0.734 mmol), and 4-iodophenol (195.3 mg, 0.888 mmol) was added. The flask was evacuated, equipped with a septum, and filled with nitrogen. DMF (10 mL) and DIPEA (0.26 mL, 1.5 mmol) were added through the septum. The reaction was stirred for 3 days and was neutralized with saturated aqueous NH4Cl (5 mL). Water (5 mL) was added and the mixture was extracted with EtOAc (3×10 mL). The combined EtOAc phases was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The product was purified with dry column vacuum chromatography (EtOAc:hexanes 1:90→90:1 v/v). The final product was white and solid (129.6 mg, 60%) Rf=0.48 (EtOAc:hexanes 1:1 v/v). 1H-NMR (DMSO-d6): □ 1.21 (t, 3H, J=7.2 Hz, CH2CH3); 4.17 (q, 2H, J=7.1 Hz, CH2CH3); 4.82 (s, 2H, OCH2); 6.78 (d, 2H, J=8.7 Hz, Ph); 6.95 (d, 2H, J=9.0 Hz, Ph); 7.34 (d, 2H, J=8.7 Hz, Ph); 7.43 (d, 2H, J=8.7 Hz, Ph); 9.67 (s, 1H, OH). 13C-NMR (DMSO-d6): □ 14.0 (CH2CH3); 60.7 (CH2CH3); 64.7 (OCH2); 87.1 (CC); 88.6 (CC); 112.8, 114.9, 115.6, 115.7, 132.6, 132.8, 157.5, 157.8 (Ph); 168.5 (COO). MALDI-MS: m/z calculated for C18H16O3 [M]+ 296.1043. found 296.1046.

Provenance & Evidence