反应 #2075719

反应方程式

HCl

n-Butyllithium

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

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

→

title compound

收率 50.7%

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

收率 50.7%

溶剂

water

diethyl ether

diethyl ether

反应条件

后处理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   其他the temperature below −70° C
3. 3
   萃取the product was then extracted with diethyl ether
4. 4
   其他The organic phase was dried
5. 5
   浓缩concentrated under vacuum

实验过程

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).

来源