Water → 3-(Methylthio)-4-nitrophenol

Participants

Reaction Steps

To a solution of 3-fluoro-4-nitrophenol (3.0 g, 19.1 mmol) in anhydrous DMF (100 mL) was added dropwise sodium thiomethoxide (2.57 mL, 38.2 mmol, 2.0 eq) followed by potassium carbonate (7.92 g, 57.3 mmol, 3.0 eq), and the reaction mixture was stirred at RT for 18 h. Water was then added to quench the solution, and the reaction mixture was extracted with EtOAc (3×250 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, and evaporated under reduced pressure. Purification of the crude using MPLC (biotage) eluted with 20% EtOAc—hexanes afforded 3.25 g (91.9%) of 3-(methylsulfanyl)4-nitrophenol as a yellow solid.

Provenance & Evidence