反応 #42270

反応方程式

Carbonyl diimidazole

3-bromo-5-(methoxycarbonyl)benzoic acid

3-Bromo-5-(methoxycarbonyl)benzoic acid

Dipropylamine

→

title compound

Methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate

溶媒

THF

反応条件

後処理

1. 1
   workup.STIRRINGis then stirred for 24 hours
2. 2
   その他The solvent is then removed under reduced pressure
3. 3
   その他the mixture is partitioned between ethyl acetate and water
4. 4
   洗浄The organic phase is then washed with saline
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated

実験手順

Carbonyl diimidazole (3.0 g, 18 mmol) is added to a solution of 3-bromo-5-(methoxycarbonyl)benzoic acid (XIX, PREPARATION 2, 3.9 g, 15 mmol) in THF (30 mL). The mixture is stirred for 0.5 hours. Dipropylamine (AMINE, 4.2 mL, 30 mmol) is added to the mixture, which is then stirred for 24 hours. The solvent is then removed under reduced pressure and the mixture is partitioned between ethyl acetate and water. The organic phase is then washed with saline, dried over anhydrous magnesium sulfate, filtered, and concentrated. Column chromatography (silica gel; ethyl acetate/hexanes, 15/85) gives the title compound, IR (diffuse reflectance) 2968, 2958, 1714, 1637, 1479, 1440, 1422, 1321, 1310, 1288, 1273, 1252, 889, 772 and 718 cm−1; NMR (300 MHz, CDCl3) δ 8.21, 7.96, 7.70, 3.95, 3.46, 3.15, 1.69, 1.57, 1.00 and 0.78; MS (ESI+) for C15H20BrNO3 m/z (M+H)+=344.1.

出典