Synthesis
1. 1-Bromo-3,5-difluorobenzene (10 g, 0.052 mol) was dissolved in anhydrous DMF (300 mL) at 0-5 °C. 2. Sodium methanol (5.60 g, 0.1036 mol) was added to the above solution. 3. The reaction mixture was stirred at room temperature for 24 h. 4. Upon completion of the reaction, the reaction mixture was extracted three times with ethyl acetate. 5. The organic layers were combined, washed with brine and then dried with anhydrous Na2SO4. 6. The solvent was removed by evaporation to give 3-bromo-5-fluoroanisole (7.5 g, 71% yield).
References
[1] Patent: US2008/261941, 2008, A1. Location in patent: Page/Page column 43
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 2, p. 758 - 766
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 11, p. 1634 - 1647
