Reaktion #42469

Reaktionsgleichung

methyl 3,5-dibromo-4-methoxybenzoate

BINAP

cesium carbonate

butylamine

→

title compound

Methyl 3-bromo-5-(butylamino)-4-methoxybenzoate

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed overnight
2. 2
   TemperaturThe mixture was cooled to room temperature
3. 3
   Filtrationfiltered through diatomaceous earth
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigePurification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes)

Vorschrift

To a stirred solution of Pd(OAc)2 (144 mg), BINAP (1.2 g), and cesium carbonate (8.4 g) in toluene (100 mL) was added butylamine (1.6 mL), and the mixture was heated at 80° C. for 15 min. A solution methyl 3,5-dibromo-4-methoxybenzoate (4.2 g) in toluene (30 mL) was added dropwise over 20 min. The mixture was refluxed overnight. The mixture was cooled to room temperature, filtered through diatomaceous earth, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes) provided 3.5 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.52, 7.19, 3.90, 3.88, 3.18, 1.66, 1.46, 0.97.

Quelle