Reacción #1833256

Ecuación de reacción

Methyl 4-amino-3-chloro-6-(2,2-difluoro-7-(trimethylsilyl)benzo[d][1,3]dioxol-4-yl)-5-fluoropicolinate

bromine

NaHSO3

→

title compound

Rendimiento 92.0%

Methyl 4-amino-6-(7-bromo-2,2-difluorobenzo[d][1,3]dioxol-4-yl)-3-chloro-5-fluoropicolinate

Rendimiento 92.0%

Disolventes

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate (35 mL)
2. 2
   LavadoThe organic phase was washed with saturated NaCl (5 mL)
3. 3
   Secadodried (Na2SO4)
4. 4
   Otroevaporated

Procedimiento

Methyl 4-amino-3-chloro-6-(2,2-difluoro-7-(trimethylsilyl)benzo[d][1,3]dioxol-4-yl)-5-fluoropicolinate (400 mg, 0.92 mmol) was stirred in 1,2-dichloroethane (5 mL), treated with bromine (1.0 g, 6.5 mmol) and stirred at 20-25° C. for 4 h. The solution was stirred with 10% NaHSO3 solution (30 mL) and extracted with ethyl acetate (35 mL). The organic phase was washed with saturated NaCl (5 mL), dried (Na2SO4) and evaporated to give the title compound as a white solid (370 mg, 92%): mp 168-170° C.; 1H NMR (400 MHz, CDCl3) δ 7.35 (m, 1H), 5.02 (s, 1H), 3.99 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −49.23, −137.58; ESIMS m/z 439 ([M+H]+), 437 ([M−H]−).

Fuente