반응 #428560

반응 방정식

DMF

4-bromomethyl-2,3-difluorobenzoic acid methyl ester

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

potassium carbonate

→

intermediate ( 8a )

수율 75.9%

4-(4-Bromo-2-butyl-5-formyl-imidazol-1-ylmethyl)-2,3-difluorobenzoic acid methyl ester

수율 75.9%

용매

water

반응 조건

후처리

1. 1
   추출extracted with EtOAc
2. 2
   세척The organic layer was washed with saturated aqueous NaCl
3. 3
   건조dried over MgSO4
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타The crude reaction
7. 7
   기타was purified by silica gel chromatography (0-50% EtOAc:hexanes)

실험 절차

4-bromomethyl-2,3-difluorobenzoic acid methyl ester (3.5 g, 13.2 mmol), 5-bromo-2-butyl-3H-imidazole-4-carbaldehyde (3.1 g, 13.2 mmol) and potassium carbonate (1.8 g, 13.2 mmol) were combined and dissolved in DMF (20 mL, 300 mmol). The mixture was stirred at room temperature overnight. The mixture was then diluted with water and extracted with EtOAc. The organic layer was washed with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated. The crude reaction was purified by silica gel chromatography (0-50% EtOAc:hexanes) to obtain 4.16 g of intermediate (8a) as a yellow solid. MS m/z: [M+H+] calcd for C17H7BrF2N2O3, 416.23; found 417.1. 1H-NMR (CDCl3): 9.68 (1H, s), 7.64 (1H, t), 6.55 (1H, t), 5.64 (2H, s), 3.95 (3H, s), 2.63 (2H, t), 1.69 (2H, m), 1.36 (2H, m) 0.90 (3H, t).

출처