반응 #171064

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5-(4-bromo-2-methyl-3-oxobutan-2-yl)-2-fluorobenzonitrile

NaN3

→

5-(4-azido-2-methyl-3-oxobutan-2-yl)-2-fluorobenzonitrile

수율 78.0%

용매

water

DMF

반응 조건

후처리

1. 1
   추출extracted with EtOAc
2. 2
   세척The combined extracts were washed with brine (100 mL)
3. 3
   건조dried over MgSO4
4. 4
   기타evaporated in vacuo
5. 5
   기타The residue was purified by flash column chromatography (silica, Hex/EtOAc=4:1)

실험 절차

To a stirred solution of 5-(4-bromo-2-methyl-3-oxobutan-2-yl)-2-fluorobenzonitrile (10 g, 35.2 mmol) in DMF (100 mL) at 0° C. was added NaN3 (2.52 g, 38.7 mmol, 1.1 eq) portionwise. After stirring 2 h, the residue was diluted with water and extracted with EtOAc. The combined extracts were washed with brine (100 mL), dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography (silica, Hex/EtOAc=4:1) to give 5-(4-azido-2-methyl-3-oxobutan-2-yl)-2-fluorobenzonitrile (6.6 g, 2 step overall yield 78%). 1H NMR (400 MHz, CDCl3) δ 7.57-7.55 (m, 1H), 7.50-7.46 (m, 1H), 7.25 (t, J=7.2 Hz, 1H), 3.8 (s, 2H), 1.55 (s, 6H).

출처