反応 #45341

反応方程式

NaHSO3

t-butyl nitrite

3-methoxy-5-(trifluoromethyl)aniline

Iodine

→

1-iodo-3-methoxy-5-(trifluoromethyl)benzene

溶媒

CHCl3

反応条件

後処理

1. 1
   温度was maintained at this temperature for an hour and thirty minutes
2. 2
   温度The reaction was then cooled to room temperature
3. 3
   抽出The mixture was extracted with EtOAc (50 mL)
4. 4
   洗浄the organic extracts were washed with aq. NaHSO3 (3×50 mL) and brine (20 mL)
5. 5
   乾燥dried over Na2SO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他Purification by flash chromatography with 1% to 15% EtOAc/hexanes

実験手順

3-methoxy-5-(trifluoromethyl)aniline (100 mg, 0.52 mmol) was dissolved in CHCl3 (5.2 mL) and t-butyl nitrite (124 μL, 1.05 mmol) was added dropwise by syringe. Iodine (266 mg, 1.05 mmol) was added and then the reaction was slowly heated to 50° C. and was maintained at this temperature for an hour and thirty minutes. The reaction was then cooled to room temperature and poured into aq. NaHSO3 (50 mL). The mixture was extracted with EtOAc (50 mL) and the organic extracts were washed with aq. NaHSO3 (3×50 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 1% to 15% EtOAc/hexanes afforded 1-iodo-3-methoxy-5-(trifluoromethyl)benzene. Rf=0.75 (25% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 7.53 (s, 1H), 7.41 (s, 1H), 7.09 (s, 1H), 3.82 (s, 3H).

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