반응 #428558

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

DMF

NBS

→

title compound

수율 17.1%

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

수율 17.1%

반응 조건

후처리

1. 1
   농축The mixture was then concentrated
2. 2
   추출The aqueous layer was extracted three times with EtOAc
3. 3
   세척the combined organic extracts washed with saturated aqueous NaCl
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The mixture was purified by silica gel chromatography (0-50% EtOAc:hexanes)

실험 절차

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).

출처