반응 #1833222

반응 방정식

5-Bromo-2,2,4-trifluorobenzo[d][1,3]dioxole

isopropylmagnesium chloride lithium chloride

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

→

title compound

수율 72.4%

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

수율 72.4%

용매

tetrahydrofuran

NH4Cl

ethyl acetate

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 1 h at 10-15° C
3. 3
   세척The organic phase was washed with saturated NaCl (15 mL)
4. 4
   건조dried (Na2SO4)
5. 5
   기타evaporated

실험 절차

5-Bromo-2,2,4-trifluorobenzo[d][1,3]dioxole (4.0 g, 16 mmol) was dissolved in 20 mL dry tetrahydrofuran, cooled to −20° C. and treated with isopropylmagnesium chloride-lithium chloride complex (1.3 M in tetrahydrofuran; 13 mL, 17 mmol) in portions over 10 min. After stirring for 30 min at −20 to 0° C., 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.1 g, 17 mmol) was added, and stirring was continued for 1 h at 10-15° C. After treatment with saturated NH4Cl solution (10 mL), the mixture was diluted with ethyl acetate (50 mL). The organic phase was washed with saturated NaCl (15 mL), dried (Na2SO4) and evaporated to give the title compound as a brown solid (3.5 g, 72%): 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=26.5 Hz, 1H), 6.90 (dd, J=18.5, 4.5 Hz, 1H), 1.35 (s, 12H); 19F NMR (376 MHz, CDCl3) δ −49.70 (s), −126.00 (s); EIMS m/z 302.

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