3-Iodophenol → HCID 66223408, compound

Participants

Reaction Conditions

Reaction Steps

3-Iodophenol (5.35 g, 24.3 mmol) was added to a suspension of NaH (1.46 g, 36.5 mmol, 60% in mineral oil) in anhydrous DMF (30 mL) at 0° C. After hydrogen evolution had ceased, 15-crown-5 (0.535 g, 2.43 mmol) and 2-bromo-1,1-dimethoxyethane (7.1 g, 42 mmol) were added. The resulting mixture was heated at 130° C. for 3 h, cooled to room temperature, poured into water (200 mL), and extracted with Et2O (3×150 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified on a silica gel column using EtOAc in petroleum ether (1:50) to afford the title compound (6.36 g, 85%). 1H NMR (DMSO-d6, 400 MHz): δ 7.32 (s, 1H), 7.30-7.26 (m, 1H), 7.07 (t, 1H), 7.00-6.94 (m, 1H), 4.66 (t, 2H), 3.98 (d, 1H), 3.33 (s, 6H).

Provenance & Evidence