反応 #1833216

反応方程式

sodium iodide

sodium nitrite

2,2,6-Trifluorobenzo[d][1,3]dioxol-5-amine

hydrochloric acid

sodium bisulfite

→

title compound

収率 51.0%

2,2,5-Trifluoro-6-iodobenzo[d][1,3]dioxole

収率 51.0%

溶媒

dichloromethane

water

water

反応条件

後処理

1. 1
   workup.STIRRINGStirring
2. 2
   workup.STIRRINGstirred for 20 min more
3. 3
   その他The phases were separated
4. 4
   抽出the aqueous phase was extracted with dichloromethane (75 mL)
5. 5
   洗浄The combined organic phases were washed with saturated NaCl (30 mL)
6. 6
   乾燥dried (Na2SO4)
7. 7
   その他evaporated
8. 8
   その他The residue was purified by chromatography on silica with hexane

実験手順

2,2,6-Trifluorobenzo[d][1,3]dioxol-5-amine (8.0 g, 42 mmol) was added to concentrated hydrochloric acid (conc. HCl; 200 mL), cooled to 5° C., vigorously stirred and treated dropwise with a solution of sodium nitrite (4.3 g, 63 mmol) in water (10 mL) over 10 min. Stirring was continued for 30 min at 5-10° C. and the mixture was poured cautiously into a solution of sodium iodide (19 g, 130 mmol) in water (200 mL), rapidly stirred with dichloromethane (100 mL). After 20 min the mixture was treated with 10% sodium bisulfite solution (NaHSO3; 20 mL) and stirred for 20 min more. The phases were separated and the aqueous phase was extracted with dichloromethane (75 mL). The combined organic phases were washed with saturated NaCl (30 mL), dried (Na2SO4) and evaporated. The residue was purified by chromatography on silica with hexane to give the title compound as a clear liquid (6 g, 51%): 1H NMR (400 MHz, CDCl3) δ 7.41 (d, J=5.0 Hz, 1H), 6.90 (d, J=6.6 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −49.63 (s), −95.24 (s); EIMS m/z 302.

出典