3-Iodophenol → Ethyl 2-(4-((3-hydroxyphenyl)ethynyl)phenoxy)acetate

Participants

Reaction Steps

To a dried Schlenk flask filled with nitrogen was added Pd(PPh3)4 (17.3 mg, 0.015 mmol), CuI (6.6 mg, 0.035 mmol), ethyl 2-(4-ethynylphenoxy)acetate (60.6 mg, 0.294 mmol), and 3-iodophenol (78.4 mg, 0.352 mmol) was added. The flask was evacuated, equipped with a septum, and filled with nitrogen. DMF (5 mL) and DIPEA (0.1 mL, 0.6 mmol) were added through the septum. The reaction was stirred over night and was neutralized with saturated aqueous ammonium chloride (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 on a dry silica column (EtOAc:hexanes 1:90→90:1 v/v). The final product was yellow/orange and solid (52 mg, 60%). Rf=0.46 (EtOAc:hexanes 1:1 v/v). 1H-NMR (DMSO-d6): □ 1.22 (t, 3H, J=7.7 Hz, CH2CH3); 4.18 (q, 2H, J=7.5 Hz, CH2CH3); 4.84 (s, 2H, OCH2); 6.9 (m, 5H, Ph); 7.20 (t, 1H, J=8.0 Hz, Ph); 7.49 (m, 2H, Ph); 9.67 (s, 1H, OH). 13C-NMR (DMSO-d6): □ 14.0 (CH2CH3); 60.7 (CH2CH3); 64.7 (OCH2); 88.3 (CC); 88.6 (CC); 115.0, 116.0, 117.6, 122.1, 123.4, 128.4, 129.8, 132.9, 157.3, 157.8 (Ph); 168.5 (COO).

Provenance & Evidence