تفاعل #1833249

معادلة التفاعل

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

المردود 84.4%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

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
   أخرىThe reaction was quenched with saturated aqueous ammonium chloride
4. 4
   استخلاصextracted three times with ethyl acetate
5. 5
   غسيلThe combined organic layers were washed with brine
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   ترشيحThe solution was filtered
8. 8
   تركيزconcentrated

الإجراء التجريبي

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.

المصدر