反応 #1994289

反応方程式

n-butyllithium

1-chloro-2,3-difluorobenzene

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

→

title compound

2-(4-Chloro-2,3-difluorophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

溶媒

THF

—

hexanes

water

ethyl acetate

反応条件

後処理

1. 1
   温度to warm to ambient temperature
2. 2
   抽出the organic phase was extracted twice with water
3. 3
   抽出The product was then extracted with ethyl acetate
4. 4
   その他The organic phase was dried
5. 5
   濃縮concentrated under vacuum

実験手順

A 2.5 M solution of n-butyllithium (2.69 ml, 6.73 mmol) in hexanes was added dropwise to a solution of 1-chloro-2,3-difluorobenzene (1 g, 6.73 mmol) in THF (25 mL) cooled to −78° C. After 45 minutes at −78° C., 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (1.253 g, 6.73 mmol) was added dropwise after which the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was diluted with water and ethyl acetate and the organic phase was extracted twice with water. The aqueous extracts were combined and acidified with 12N HCl to pH 3. The product was then extracted with ethyl acetate. The organic phase was dried and concentrated under vacuum to yield the title compound as an oil product (0.93 g, 50% yield): 1H NMR (CDCl3): δ 7.42 (m, 1H), 7.17 (m, 1H), 1.37 (s, 12H).

出典