반응 #1833218

반응 방정식

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

Sec-Butyllithium

iodine

→

title compound

수율 58.4%

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

수율 58.4%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The solution was cooled to −75° C.
2. 2
   온도the mixture was cooled to −75° C
3. 3
   workup.STIRRINGThe mixture was stirred for 1 h during which time the temperature
4. 4
   기타rose to −20° C
5. 5
   기타The reaction was quenched by addition of saturated NH4Cl (10 mL)
6. 6
   세척The organic phase was washed with saturated NaCl (10 mL)
7. 7
   건조dried (Na2SO4)
8. 8
   기타evaporated
9. 9
   기타The material was purified by flash chromatography with hexane

실험 절차

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.

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