Reacción #1833220

Ecuación de reacción

5-Bromo-4-chloro-2,2-difluorobenzo[d][1,3]dioxole

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

→

title compound

Rendimiento 101.8%

2-(4-Chloro-2,2-difluorobenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Rendimiento 101.8%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONtreated in portions with isopropylmagnesium chloride-lithium chloride complex solution (1.3 M; 3.1 mL, 4.1 mmol)
2. 2
   workup.WAITwas continued at 0-20° C. for 90 min
3. 3
   OtroThe reaction was quenched by addition of saturated NH4Cl (10 mL)
4. 4
   Extracciónthe mixture was extracted with ethyl acetate (30 mL)
5. 5
   ExtracciónThe aqueous phase was extracted again with ethyl acetate (15 mL)
6. 6
   Lavadothe combined organic phases were washed with saturated NaCl (15 mL)
7. 7
   Secadodried (Na2SO4)
8. 8
   Otroevaporated

Procedimiento

5-Bromo-4-chloro-2,2-difluorobenzo[d][1,3]dioxole (1.0 g, 3.7 mmol) was dissolved in dry tetrahydrofuran (12 mL), cooled to −20 to −30° C. and treated in portions with isopropylmagnesium chloride-lithium chloride complex solution (1.3 M; 3.1 mL, 4.1 mmol). After 90 min at −20 to 0° C., 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (830 μL, 750 mg, 4.1 mmol) was added, and stirring was continued at 0-20° C. for 90 min. The reaction was quenched by addition of saturated NH4Cl (10 mL), and the mixture was extracted with ethyl acetate (30 mL). The aqueous phase was extracted again with ethyl acetate (15 mL), and the combined organic phases were washed with saturated NaCl (15 mL), dried (Na2SO4) and evaporated to give the title compound as a white solid (1.2 g, ca. 100%): 1H NMR (400 MHz, CDCl3) δ 7.52 (d, J=8.1 Hz, 1H), 6.99-6.94 (m, 1H), 1.36 (s, 12H); 19F NMR (376 MHz, CDCl3) δ −49.62 (s); EIMS m/z 318.

Fuente