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116 ml (116 mmol) of boron tribromide (1 molar solution in dichloromethane) are added dropwise at -10° C. over a period of 1 h to a solution of 5.00 g (29.2 mmol) of <strong>[454-16-0]1-fluoro-2-methoxy-4-nitrobenzene</strong> at such a rate that the temperature does not exceed -5° C. The solution is left at 0° C. for 5 h, then added slowly to 600 ml of ice-water and diluted with 100 ml of ethyl acetate. After phase separation, the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate. After filtration, the solvents are removed under reduced pressure. The residue is purified by chromatography on silica gel (10:1 cyclohexane/ethyl acetate). This affords 1.45 g (30percent of theory) of the desired compound. 1H NMR (400 MHz, DMSO-d6, delta/ppm): 10.99 (s, 1H), 7.78 (dd, 1H), 7.73 (ddd, 1H), 7.44 (dd, 1H). HPLC (Method 1): Rt=3.60 min. MS (DCI, m/z): 174 (M+NH4)+.
To a solution of 2-fluoro-5-nitrophenol (5.0 g, 31.84 mmol) in DMF(50 mL) was added K2C03 (5.27 g, 38.1 mmol), after stirring at room temperature for 15 mm was added methyliodide (3 mL, 47.7 mmol) and the reaction mixture stirred at room temperature for 2h. Reaction mixture was poured into ice water, separated solids were filtered, washed the solid thoroughly with water and vacuum dried to afford an off white solid (4.0 g, 73.5percent). 1H NMR (300 MHz, CDC13) 7.89-7.84 (m, 2H), 7.25-7. 17 (m, 1H), 3.98 (s, 3H).
73.5%
Step-a Synthesis of 1-fluoro-2-methoxy-4-nitrobenzene To a solution of 2-fluoro-5-nitrophenol (5.0 g, 31.84 mmol) in DMF (50 mL) was added K2CO3 (5.27 g, 38.1 mmol), after stirring at room temperature for 15 min was added methyl iodide (3 mL, 47.7 mmol) and the reaction mixture stirred at room temperature for 2 h. Reaction mixture was poured into ice water, separated solids were filtered, washed the solid thoroughly with water and vacuum dried to afford an off white solid (4.0 g, 73.5percent). 1H NMR (300 MHz, CDCl3): 7.89-7.84 (m, 2H), 7.25-7.17 (m, 1H), 3.98 (s, 3H).
With potassium carbonate; In acetonitrile; for 2h;Reflux;
1.57 g 2-Fluoro-5-nitrophenol (10 mmol) was dissolved in 50 ml dry acetonitrile. 2.07 g potassium carbonate (15 mmol) and 1.70 g iodomethane (12 mmol) were added. The mixture was refluxed for 2 hours. Then it was poured onto 100 g ice and the mixture was extracted three times with 40-40 ml ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4 and evaporated under reduced pressure. Residue was crystallized upon cooling and was used without any further purification or analytical investigation. Yield: 1.62 g (95percent).
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