反応 #45324

反応方程式

2-Amino-5-(trifluoromethyl)benzonitrile

t-butyl nitrite

CH2I2

→

2-Iodo-5-(trifluoromethyl)benzonitrile

溶媒

反応条件

後処理

1. 1
   温度was maintained at this temperature for 30 minutes
2. 2
   温度The reaction was then cooled to room temperature
3. 3
   その他purified with 100% hexanes to 15% EtOAc/hexanes
4. 4
   その他were removed by silica gel chromatography with 25% CH2Cl2/hexanes

実験手順

2-Amino-5-(trifluoromethyl)benzonitrile (3.06 g, 16.45 mmol) was suspended in CH2I2 (36 mL) and t-butyl nitrite (3.9 mL, 32.9 mmol) was added dropwise by syringe. The reaction was heated slowly to 100° C. and was maintained at this temperature for 30 minutes. The reaction was then cooled to room temperature, diluted with hexanes (200 mL), loaded on a silica gel column, and purified with 100% hexanes to 15% EtOAc/hexanes. The resulting product, 2-iodo-5-(trifluoromethyl)benzonitrile was contaminated with minor impurities which were removed by silica gel chromatography with 25% CH2Cl2/hexanes. 2-Iodo-5-(trifluoromethyl)benzonitrile was obtained as a white solid. Rf=0.44 (15% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 8.10 (d, J=8.5 Hz, 1H), 7.85 (d, J=1.8 Hz, 1H), 7.52 (dd, J=8.5, 1.8 Hz, 1H).

出典