(4-溴-2-氟苯基) 乙酸甲酯

反应条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: AlCl3 (5.0 g, 38 mmol) was added in portions to 4-bromo-2-fluorophenyl acetate (5.8 g, 25 mmol). The mixture was heated at 150° C. for 3 h and then brought to ambient temperature. Water (ice-cold) was slowly added and then EtOAc. The resulting mixture was vigorously stirred and then the phases were separated and the water phase extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness to give the title compound (5.3 g). MS m/z (rel. intensity, 70 eV) 233 (M+, 55), 232 (M+, 56), 218 (98), 217 (bp), 161 (10). brought to ambient temperature the phases were separated the water phase extracted with EtOAc The combined organic phases were washed with brine dried (Na2SO4) evaporated to dryness

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 4-bromo-2-fluorophenol (5 g, 30 mmol) and acetic anhydride (13.4 g, 130 mmol) in pyridine (10.6 ml, 130 mmol) was heated at 100° C. for 3 h and then brought to ambient temperature and poured into water. HCl (1 N and 6 N) was added and the solution was extracted with EtOAc. The combined organic phases were washed with sodium bicarbonate (saturated, 3×50 ml), dried (Na2SO4) and evaporated to dryness to give the title compound (5.8 g). MS m/z (rel. intensity, 70 eV) 233 (M+, 11), 232 (M+, 12), 191 (95), 190 (bp), 161 (8). brought to ambient temperature was added the solution was extracted with EtOAc The combined organic phases were washed with sodium bicarbonate (saturated, 3×50 ml) dried (Na2SO4) evaporated to dryness

反应条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: AlCl3 (5.0 g, 38 mmol) was added in portions to 4-bromo-2-fluorophenyl acetate (5.8 g, 25 mmol). The mixture was heated at 150° C. for 3 h and then brought to ambient temperature. Water (ice-cold) was slowly added and then EtOAc. The resulting mixture was vigorously stirred and then the phases were separated and the water phase extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness to give the title compound (5.3 g). MS m/z (rel. intensity, 70 eV) 233 (M+, 55), 232 (M+, 56), 218 (98), 217 (bp), 161 (10). brought to ambient temperature the phases were separated the water phase extracted with EtOAc The combined organic phases were washed with brine dried (Na2SO4) evaporated to dryness

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 4-bromo-2-fluorophenol (5 g, 30 mmol) and acetic anhydride (13.4 g, 130 mmol) in pyridine (10.6 ml, 130 mmol) was heated at 100° C. for 3 h and then brought to ambient temperature and poured into water. HCl (1 N and 6 N) was added and the solution was extracted with EtOAc. The combined organic phases were washed with sodium bicarbonate (saturated, 3×50 ml), dried (Na2SO4) and evaporated to dryness to give the title compound (5.8 g). MS m/z (rel. intensity, 70 eV) 233 (M+, 11), 232 (M+, 12), 191 (95), 190 (bp), 161 (8). brought to ambient temperature was added the solution was extracted with EtOAc The combined organic phases were washed with sodium bicarbonate (saturated, 3×50 ml) dried (Na2SO4) evaporated to dryness

反应条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: AlCl3 (5.0 g, 38 mmol) was added in portions to 4-bromo-2-fluorophenyl acetate (5.8 g, 25 mmol). The mixture was heated at 150° C. for 3 h and then brought to ambient temperature. Water (ice-cold) was slowly added and then EtOAc. The resulting mixture was vigorously stirred and then the phases were separated and the water phase extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness to give the title compound (5.3 g). MS m/z (rel. intensity, 70 eV) 233 (M+, 55), 232 (M+, 56), 218 (98), 217 (bp), 161 (10). brought to ambient temperature the phases were separated the water phase extracted with EtOAc The combined organic phases were washed with brine dried (Na2SO4) evaporated to dryness

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 4-bromo-2-fluorophenol (5 g, 30 mmol) and acetic anhydride (13.4 g, 130 mmol) in pyridine (10.6 ml, 130 mmol) was heated at 100° C. for 3 h and then brought to ambient temperature and poured into water. HCl (1 N and 6 N) was added and the solution was extracted with EtOAc. The combined organic phases were washed with sodium bicarbonate (saturated, 3×50 ml), dried (Na2SO4) and evaporated to dryness to give the title compound (5.8 g). MS m/z (rel. intensity, 70 eV) 233 (M+, 11), 232 (M+, 12), 191 (95), 190 (bp), 161 (8). brought to ambient temperature was added the solution was extracted with EtOAc The combined organic phases were washed with sodium bicarbonate (saturated, 3×50 ml) dried (Na2SO4) evaporated to dryness

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The synthesis was performed using a crude product obtained by synthesis using 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(t rifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one synthesized in Reference Synthesis Example 346 and 4-bromo-2-fluorophenyl acetate in a similar manner to Reference Synthesis Example 139, in a similar manner to Reference Synthesis Example 2 (two step yield 41%). obtained by synthesis