Chemical Properties
Yellow powder
Uses
4-Fluoro-2-nitroanisole is formed during the photolysis of the charge transfer complex of tetranitromethane and 4-fluoroanisole in dichloromethane at -20°C.
General Description
4-Fluoro-2-nitroanisole is formed during the photolysis of the charge transfer complex of tetranitromethane and 4-fluoroanisole in dichloromethane at -20°C.
Synthesis
General procedure for the synthesis of 2-nitro-4-fluoroanisole from 2-nitro-4-fluorophenol and iodomethane: Acetonitrile (100 mL) solution of iodomethane (127.8 g, 0.9004 mol) was added slowly and dropwise to an acetonitrile (450 mL) solution containing 5-fluoro-2-nitrophenol (94.2 g, 0.600 mol) and potassium carbonate (207 g, 1.50 mol). mL) solution. The reaction mixture was heated to reflux for 15 hours. Upon completion of the reaction, the mixture was cooled to room temperature, filtered to remove insoluble solids, and the filter cake was washed twice with dichloromethane (100 mL). The filtrate and washings were combined and the solvent was evaporated to dryness by rotary evaporator to afford the crude product 2-nitro-4-fluoroanisole (96 g, 0.56 mol, 93% yield), which could be used in subsequent reactions without further purification.
References
[1] Patent: WO2005/26137, 2005, A2. Location in patent: Page/Page column 230-231
[2] Synthetic Communications, 1989, vol. 19, # 1, 2, p. 233 - 238
