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

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.

1. temperatureThe mixture was heated to reflux
2. customthe solvent volume reduced to 5 mL by evaporation under reduced pressure
3. extractionextracted with diethyl ether (3×40 mL)
4. washwashed with saturated sodium chloride solution
5. dry with materialdried over sodium sulfate
6. customthe volatiles were removed by evaporation under reduced pressure
7. customThe product was purified by silica gel chromatography

ORD record

ord-9f464fbd9f9947e9a0f8af1ef23368a2

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884801B1