2,6-Difluorophenol → HCID 136088166, compound

Participants

Reaction Steps

4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)aniline (17) (0.436 g, 1.71 mmol) was dissolved in hot mixture of 20 mL of water and 0.5 mL of conc. HCl. The solution was cooled in ice/NaCl bath to 0° C. and then the solution of sodium nitrite (0.140 g, 2.03 mmol in 4 mL of water) was added dropwise to the solution of ammonium salt, maintaining the temperature below +5° C. The resulting solution of diazonium salt was stirred for 30 min and then added dropwise to the solution of 2,6-difluorophenol (0.220 g, 1.69 mmol) in 10 mL of 1M KOH, cooled in ice/water bath. The reaction mixture was stirred for 40 min in ice/water bath and then acidified with 10% HCl to pH 2-3 and extracted with ethyl acetate (4×40 mL). The combined extract was washed with brine (30 mL), dried over Na2SO4 and evaporated. The crude product was purified by column chromatography on silica gel using 2:1 chloroform-ethyl acetate mixture as an eluant to give phenol 18 as a orange solid (0.094 g, 14%).

Provenance & Evidence