Phenol → 5-Phenoxy-2-benzofuran-1(3H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-3H-isobenzofuran-1-one (75.9 g, 0.36 mol) (Sigma-Aldrich), phenol (67.1 g, 0.713 mol), CuCl (17.6 g, 0.178 mol), 2,2,6,6-tetramethyl-heptane-3,5-dione (TMHD, 7.33 mL) and cesium carbonate (232.3 g, 0.713 mol) in NMP (200 mL) was heated at 130° C. for 64 h. After cooled, reaction mixture was poured into ice/2M HCl mixture (1 L). The mixture was then refluxed for 1 h. After cooled, the solid was collected, rinsed with water and dried in vacuo to provide the title compound (72.22 g, 0.32 mol). 1H NMR in DMSO-d6, δ in ppm: 7.82 (dd, 1H, J=1.6 Hz, 7.6 Hz), 7.51-7.40 (m, 2H), 7.3-7.1 (m, 5H), 5.31 (s, 2H).

Provenance & Evidence