Reacción #1833249

Ecuación de reacción

5-bromo-2,2-difluorobenzo[d][1,3]dioxole

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

→

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

Rendimiento 84.4%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONIsopropylmagnesium chloride-lithium chloride complex (1.3 M; 10 mL, 13.0 mmol) was added slowly
2. 2
   workup.STIRRINGthe reaction mixture was stirred for 1 h
3. 3
   OtroThe reaction was quenched with saturated aqueous ammonium chloride
4. 4
   Extracciónextracted three times with ethyl acetate
5. 5
   LavadoThe combined organic layers were washed with brine
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   FiltraciónThe solution was filtered
8. 8
   Concentraciónconcentrated

Procedimiento

To an oven-dried three-necked round bottom flask under nitrogen was added 5-bromo-2,2-difluorobenzo[d][1,3]dioxole (2.516 g, 10.6 mmol) and anhydrous tetrahydrofuran (26 mL). The solution was cooled to 0° C. Isopropylmagnesium chloride-lithium chloride complex (1.3 M; 10 mL, 13.0 mmol) was added slowly and stirred for 1 h. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.2 mL, 10.62 mmol) was added, and the reaction mixture was stirred for 1 h. The reaction was quenched with saturated aqueous ammonium chloride and extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solution was filtered and concentrated to provide 2-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a yellow oil (2.54 g, 84%): 1H NMR (400 MHz, CDCl3) δ 7.56 (dd, J=8.0, 1.0 Hz, 1H), 7.47 (d, J=0.6 Hz, 1H), 7.06 (dd, J=7.9, 0.4 Hz, 1H), 1.34 (s, 12H); 19F NMR (376 MHz, CDCl3) δ −50.18; EIMS m/z 284.

Fuente