反応 #1833218

反応方程式

2,2,5-trifluorobenzo[d][1,3]dioxole

Sec-Butyllithium

iodine

→

title compound

収率 58.4%

2,2,5-Trifluoro-4-iodobenzo[d][1,3]dioxole

収率 58.4%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度The solution was cooled to −75° C.
2. 2
   温度the mixture was cooled to −75° C
3. 3
   workup.STIRRINGThe mixture was stirred for 1 h during which time the temperature
4. 4
   その他rose to −20° C
5. 5
   その他The reaction was quenched by addition of saturated NH4Cl (10 mL)
6. 6
   洗浄The organic phase was washed with saturated NaCl (10 mL)
7. 7
   乾燥dried (Na2SO4)
8. 8
   その他evaporated
9. 9
   その他The material was purified by flash chromatography with hexane

実験手順

Sec-Butyllithium (1.4 M in cyclohexane; 6.1 mL, 8.5 mmol) was added to dry tetrahydrofuran (15 mL) which had been pre-cooled to −40° C. The solution was cooled to −75° C., treated with 2,2,5-trifluorobenzo[d][1,3]dioxole (1.5 g, 8.5 mmol) and stirred at this temperature for 90 min. This solution was rapidly transferred via cannula into a stirred solution of iodine (2.8 g, 11 mmol) in tetrahydrofuran (25 mL), and the mixture was cooled to −75° C. The mixture was stirred for 1 h during which time the temperature rose to −20° C. The reaction was quenched by addition of saturated NH4Cl (10 mL) and then combined with 10% NaHSO3 (15 mL) and ethyl acetate (30 mL). The organic phase was washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated. The material was purified by flash chromatography with hexane to give the title compound as a clear liquid (1.5 g, 58%): 1H NMR (400 MHz, CDCl3) δ 6.97 (dd, J=8.8, 4.0 Hz, 1H), 6.81 (dd, J=11.7, 5.4 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −49.06, −103.15; EIMS m/z 302.

出典