Reacción #1833237

Ecuación de reacción

NH4Cl

2,2-Difluoro-5-iodo-6-methoxybenzo[d][1,3]dioxole

isopropylmagnesium lithium chloride

NaCl

2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

→

title compound

2-(2,2-Difluoro-6-methoxybenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Disolventes

tetrahydrofuran

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITwas continued for 40 min at 15-20° C
2. 2
   LavadoThe organic phase was washed with saturated NaCl (10 mL)
3. 3
   Secadodried (Na2SO4)
4. 4
   Otroevaporated

Procedimiento

2,2-Difluoro-5-iodo-6-methoxybenzo[d][1,3]dioxole (1.6 g, 5.0 mmol) was dissolved in dry tetrahydrofuran (15 mL), cooled to 0-5° C. and treated in portions with isopropylmagnesium lithium chloride (1.3 M; 4.1 mL, 5.3 mmol). After 50 min, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.0 g, 5.4 mmol) was added and stirring was continued for 40 min at 15-20° C. The mixture was treated with saturated NH4Cl (10 mL) and then mixed with saturated NaCl (10 mL) and ethyl acetate (20 mL). The organic phase was washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated to give title compound as a thick oil which was used without further purification (1.4 g, 89%): 1H NMR (400 MHz, CDCl3) δ 7.35 (s, 1H), 6.65 (s, 1H), 3.81 (s, 3H), 1.34 (s, 12H); 19F NMR (376 MHz, CDCl3) δ −50.17 (s); EIMS m/z 314.

Fuente