反应详情

温度

65 °C

To a solution of 3-fluoro-5-methylbenzoic acid (1.50 g, 9.73 mmol, Oakwood) in Acetone (40 mL) was added Potassium carbonate (1.34 g, 9.73 mmol) followed by Methyl iodide (0.73 mL, 12 mmol). The reaction mixture was heated to 65° C. for 1 hour, heating discontinued and stirred overnight, then heating resumed at that temperature for a further 2 hours. Additional Methyl iodide (0.5 mL, 8 mmol) was added and heating was continued for 6 hours. Solids were removed by filtration and acetone was removed in vacuo. The residue was partitioned between 1N NaOH and ethyl acetate. The aqueous portion was extracted with a further two portions of ethyl acetate. The combined extracts were washed with brine, then dried over sodium sulfate, decanted and concentrated. The product so obtained was used without further purification (1.64 g, 100%). 1H NMR (300 MHz, CDCl3): δ 7.66-7.63 (m, 1H), 7.51 (d, 1H), 7.10-7.04 (m, 1H), 3.91 (s, 3H), 2.40 (s, 3H).

1. temperatureheating
2. temperatureheating
3. waitresumed at that temperature for a further 2 hours
4. temperatureheating
5. waitwas continued for 6 hours
6. customSolids were removed by filtration and acetone
7. customwas removed in vacuo
8. customThe residue was partitioned between 1N NaOH and ethyl acetate
9. extractionThe aqueous portion was extracted with a further two portions of ethyl acetate
10. washThe combined extracts were washed with brine
11. dry with materialdried over sodium sulfate
12. customdecanted
13. concentrationconcentrated
14. customThe product so obtained
15. customwas used without further purification (1.64 g, 100%)