Reacción #1994289

Ecuación de reacción

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

Disolventes

THF

—

hexanes

water

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to ambient temperature
2. 2
   Extracciónthe organic phase was extracted twice with water
3. 3
   ExtracciónThe product was then extracted with ethyl acetate
4. 4
   OtroThe organic phase was dried
5. 5
   Concentraciónconcentrated under vacuum

Procedimiento

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).

Fuente