Potassium Hydroxide → 3-fluoro-2-(methylthio)aniline

Participants

Reaction Steps

N-(2-Methylthio-3-fluorophenyl)trifluoroacetamide (2.36 g crude, 9.33 mmol, prepared as described by McKittrick, J. Het. Chem. 1990, 27, 2151-2163) was taken up in methanol (40 mL), and solid potassium hydroxide (1.57 g, 28.0 mmol) was added portionwise at room temperature. The mixture was heated to reflux. After 1.5 hours, the mixture was cooled to room temperature, and the solvent volume reduced to 5 mL by evaporation under reduced pressure. The residue was taken up in deionized water (30 mL) and extracted with diethyl ether (3×40 mL). The extracts were combined, washed with saturated sodium chloride solution, dried over sodium sulfate, and the volatiles were removed by evaporation under reduced pressure. The product was purified by silica gel chromatography using 10% ethyl acetate in hexanes. 1.2 g of 3-fluoro-2-(methylthio)aniline was isolated.

Provenance & Evidence