Reaktion #428558

Reaktionsgleichung

2-Butyl-3H-imidazole-4-carbaldehyde

DMF

NBS

→

title compound

Ausbeute 17.1%

5-Bromo-2-butyl-3H-imidazole-4-carbaldehyde

Ausbeute 17.1%

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was then concentrated
2. 2
   ExtraktionThe aqueous layer was extracted three times with EtOAc
3. 3
   Waschenthe combined organic extracts washed with saturated aqueous NaCl
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe mixture was purified by silica gel chromatography (0-50% EtOAc:hexanes)

Vorschrift

2-Butyl-3H-imidazole-4-carbaldehyde (30.0 g, 197 mmol) was dissolved in DMF (220 mL, 2.8 mol). NBS (36.8 g, 207 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was then concentrated and taken up in EtOAc and water. The aqueous layer was extracted three times with EtOAc, and the combined organic extracts washed with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated. The mixture was purified by silica gel chromatography (0-50% EtOAc:hexanes) to obtain 7.8 g of the title compound as a gray solid. MS m/z: [M+H+] calcd for C8H11BrN2O, 232.09; found 233.0. 1H-NMR (DMSO): 13.3 (1H, br), 9.48 (1H, s), 2.66 (2H, t), 1.59 (2H, m), 1.25 (2H, m), 0.85 (3H, t).

Quelle