Реакция #1833222

Уравнение реакции

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

isopropylmagnesium chloride lithium chloride

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

→

title compound

Выход 72.4%

4,4,5,5-Tetramethyl-2-(2,2,4-trifluorobenzo[d][1,3]dioxol-5-yl)-1,3,2-dioxaborolane

Выход 72.4%

Растворители

tetrahydrofuran

NH4Cl

ethyl acetate

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 1 h at 10-15° C
3. 3
   ПромывкаThe organic phase was washed with saturated NaCl (15 mL)
4. 4
   Сушкаdried (Na2SO4)
5. 5
   Другоеevaporated

Методика

5-Bromo-2,2,4-trifluorobenzo[d][1,3]dioxole (4.0 g, 16 mmol) was dissolved in 20 mL dry tetrahydrofuran, cooled to −20° C. and treated with isopropylmagnesium chloride-lithium chloride complex (1.3 M in tetrahydrofuran; 13 mL, 17 mmol) in portions over 10 min. After stirring for 30 min at −20 to 0° C., 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.1 g, 17 mmol) was added, and stirring was continued for 1 h at 10-15° C. After treatment with saturated NH4Cl solution (10 mL), the mixture was diluted with ethyl acetate (50 mL). The organic phase was washed with saturated NaCl (15 mL), dried (Na2SO4) and evaporated to give the title compound as a brown solid (3.5 g, 72%): 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=26.5 Hz, 1H), 6.90 (dd, J=18.5, 4.5 Hz, 1H), 1.35 (s, 12H); 19F NMR (376 MHz, CDCl3) δ −49.70 (s), −126.00 (s); EIMS m/z 302.

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