Reaktion #541671

Reaktionsgleichung

sodium carbonate

2-methoxyphenylboronic acid

tert-butyl 4-bromo-2-nitrobenzoate

citric acid

→

tert-butyl 4-(2-methoxyphenyl)-2-nitrobenzoate

Ausbeute 100.9%

Lösungsmittel

ethylene glycol dimethyl ether

Water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby heating
2. 2
   Temperaturto reflux under a nitrogen atmosphere for 2 hours and 30 minutes
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with a saturated aqueous solution of sodium chloride
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Sonstigethe solvent was evaporated under reduced pressure
7. 7
   SonstigeThe obtained residue was purified by silica gel column chromatography [eluent: 99-91% hexane/ethyl acetate]

Vorschrift

Water (9.0 mL), sodium carbonate (2.6 g), 2-methoxyphenylboronic acid (1.8 g), and bis(triphenylphosphine)palladium(II) dichloride (0.14 g) were added to an ethylene glycol dimethyl ether (30 mL) solution of tert-butyl 4-bromo-2-nitrobenzoate (3.0 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 99-91% hexane/ethyl acetate] to obtain 3.3 g of tert-butyl 4-(2-methoxyphenyl)-2-nitrobenzoate as a light yellow oily substance.

Quelle