Реакция #2075719

Уравнение реакции

HCl

n-Butyllithium

4-Bromo-1-chloro-2-(1-fluoroethyl)benzene

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

→

title compound

Выход 50.7%

2-[4-Chloro-3-(1-fluoro-ethyl)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Выход 50.7%

Растворители

water

diethyl ether

diethyl ether

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Другоеthe temperature below −70° C
3. 3
   Экстракцияthe product was then extracted with diethyl ether
4. 4
   ДругоеThe organic phase was dried
5. 5
   Концентрированиеconcentrated under vacuum

Методика

4-Bromo-1-chloro-2-(1-fluoroethyl)benzene (2.55 g, 10.74 mmol) was dissolved in dry diethyl ether (50 mL) and cooled to −75° C. n-Butyllithium (4.72 mL, 11.81 mmol) was added dropwise keeping the temperature below −70° C. The reaction mixture was then stirred for 15 min, then 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.197 g, 11.81 mmol) was added and the reaction mixture was allowed to warm to room temperature. The reaction mixture was then diluted with water and diethyl ether. The aqueous phase was acidified with 12N HCl and the product was then extracted with diethyl ether. The organic phase was dried and concentrated under vacuum to yield the title compound (1.55 g, 5.45 mmol, 50.7% yield) as a white solid: 1H NMR (CDCl3): δ 7.94 (d, 1H), 7.65 (m, 1H), 7.36 (m, 1H), 5.96 (dq, 1H), 1.64 (dd, 3H), 1.34 (s, 12H).

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