Реакция #1833220

Уравнение реакции

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

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

→

title compound

Выход 101.8%

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

Выход 101.8%

Растворители

tetrahydrofuran

Условия реакции

Обработка

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
   ДругоеThe reaction was quenched by addition of saturated NH4Cl (10 mL)
4. 4
   Экстракцияthe mixture was extracted with ethyl acetate (30 mL)
5. 5
   ЭкстракцияThe aqueous phase was extracted again with ethyl acetate (15 mL)
6. 6
   Промывкаthe combined organic phases were washed with saturated NaCl (15 mL)
7. 7
   Сушкаdried (Na2SO4)
8. 8
   Другоеevaporated

Методика

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.

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