Triethylamine → N-(3-bromo-4-(2,4-difluorophenoxy)phenyl)ethanesulfonamide

Participants

Reaction Steps

3-Bromo-4-(2,4-difluorophenoxy)aniline (3.24 g, 10.80 mmol) and triethylamine (4.37 g, 43.2 mmol) were stirred in dichloromethane (48.1 mL) at ambient temperature. Ethanesulfonyl chloride (4.16 g, 32.4 mmol) was added dropwise and the solution stirred at ambient temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, dioxane (24 mL) and sodium hydroxide (10% w/v, 12 mL, 0.427 mmol) were added, and the solution was heated to 70° C. for 1 hour. The solution was neutralized to a pH of about 7 with saturated aqueous NH4Cl (200 mL). The aqueous phase was extracted with ethyl acetate (3×125 mL). The combined organics were washed with brine, dried (anhydrous MgSO4), filtered, and then concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 0-50% ethyl acetate/petroleum ether gradient,) to afford N-(3-bromo-4-(2,4-difluorophenoxy)phenyl)ethanesulfonamide (1.4 g, 3.57 mmol, 33.1% yield).

Provenance & Evidence