反応 #42469

反応方程式

methyl 3,5-dibromo-4-methoxybenzoate

BINAP

cesium carbonate

butylamine

→

title compound

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

溶媒

toluene

toluene

反応条件

後処理

1. 1
   温度The mixture was refluxed overnight
2. 2
   温度The mixture was cooled to room temperature
3. 3
   ろ過filtered through diatomaceous earth
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他Purification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes)

実験手順

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.

出典