1112210-82-8

1435-51-4

67-63-0

1112210-82-8

Synthesis of Intermediate Ia: 60% NaH mineral oil dispersion (1.89 g, 47.25 mmol) was slowly added dropwise to anhydrous DMF (20 mL) at 0 °C and protected by inert atmosphere. Isopropanol (3.62 mL, 47.25 mmol) was then added and the mixture was stirred at 0 °C for 15 min. Next, a solution of 1,3-dibromo-5-fluorobenzene (1.98 mL, 15.75 mmol) in anhydrous DMF (20 mL) was added dropwise at the same temperature. The reaction mixture was brought to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the reaction was quenched by slow addition of saturated NaHCO3 solution and the crude product was extracted twice with ether (Et2O). The organic layers were combined, washed sequentially with saturated NaHCO3 solution three times and saturated NaCl solution once, dried over anhydrous MgSO4 and concentrated to give yellow oil Ia in quantitative yield.1H NMR (300 MHz, CDCl3) δ 7.11 (t, J = 1.4 Hz, 1H), 6.97 (d, J = 1.5 Hz, 2H), 4.61- 4.40 (m, 1H), 1.32 (d, J = 6.0 Hz, 6H).