반응 #1833217

반응 방정식

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

2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

→

title compound

수율 100.3%

4,4,5,5-Tetramethyl-2-(2,2,6-trifluorobenzo[d][1,3]dioxol-5-yl)-1,3,2-dioxaborolane

수율 100.3%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONtreated with isopropylmagnesiumchloride-lithium chloride complex solution (1.3 M; 2.7 mL, 3.5 mmol)
2. 2
   workup.STIRRINGstirred for 20 min
3. 3
   기타The reaction was quenched by addition of saturated ammonium chloride (NH4Cl; 5 mL)
4. 4
   workup.ADDITIONmixed with ethyl acetate (20 mL) and saturated NaCl (10 mL)
5. 5
   세척The separated organic phase was washed with saturated NaCl (10 mL)
6. 6
   건조dried (Na2SO4)
7. 7
   기타evaporated

실험 절차

2,2,5-Trifluoro-6-iodobenzo[d][1,3]dioxole (1.0 g, 3.3 mmol) was dissolved in dry tetrahydrofuran (10 mL), cooled to 5° C. and treated with isopropylmagnesiumchloride-lithium chloride complex solution (1.3 M; 2.7 mL, 3.5 mmol). The mixture was stirred for 1 h at 5-15° C., treated with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (720 μL, 660 mg, 3.5 mmol) and stirred for 20 min. The reaction was quenched by addition of saturated ammonium chloride (NH4Cl; 5 mL) and mixed with ethyl acetate (20 mL) and saturated NaCl (10 mL). The separated organic phase was washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated to give the title compound as a white solid (1.0 g, 100%): 1H NMR (400 MHz, CDCl3) δ 7.37 (d, J=4.3 Hz, 1H), 6.81 (d, J=7.7 Hz, 1H), 1.35 (s, 12H); 19F NMR (376 MHz, CDCl3) δ −49.96 (s), −104.21 (s)); EIMS m/z 302.

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