Reaktion #70277

Reaktionsgleichung

ethyl 5-bromo-2-chlorobenzoate

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

Cs2CO3

CH2Cl2

→

expected product

Ausbeute 92.0%

Ethyl 2-chloro-5-cyclopropylbenzoate

Ausbeute 92.0%

Lösungsmittel

dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   Extraktionthe mixture was extracted between ethyl acetate and water
3. 3
   SonstigeThe crude mixture was purified by chromatography over SiO2
4. 4
   Wascheneluting hexane/ethyl acetate mixtures

Vorschrift

In a schlenck tube, a mixture of ethyl 5-bromo-2-chlorobenzoate (7.60 mmol, 2 g), 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.59 mmol, 1.3 g), Cs2CO3 (18.97 mmol, 6.18 g), PdCl2dppf.CH2Cl2 (0.76 mmol, 0.620 g) in dioxane (70 ml) and water (15 ml) was heated for 2 hours at 110° C., under argon atmosphere. The solvent was evaporated and the mixture was extracted between ethyl acetate and water. The crude mixture was purified by chromatography over SiO2 eluting hexane/ethyl acetate mixtures and affording 1.5 g (yield 92%) of the expected product.

Quelle