Reaktion #2075720

Reaktionsgleichung

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

Lösungsmittel

THF

—

hexanes

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to ambient temperature
2. 2
   Extraktionand the organic phase was extracted twice with water
3. 3
   ExtraktionThe product was then extracted with ethyl acetate
4. 4
   SonstigeThe organic phase was dried
5. 5
   Einengenconcentrated under vacuum

Vorschrift

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 min 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).

Quelle