反応 #171064

反応方程式

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

NaN3

→

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

収率 78.0%

溶媒

water

DMF

反応条件

後処理

1. 1
   抽出extracted with EtOAc
2. 2
   洗浄The combined extracts were washed with brine (100 mL)
3. 3
   乾燥dried over MgSO4
4. 4
   その他evaporated in vacuo
5. 5
   その他The residue was purified by flash column chromatography (silica, Hex/EtOAc=4:1)

実験手順

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).

出典