Réaction #1833217

Équation de réaction

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

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

→

title compound

Rendement 100.3%

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

Rendement 100.3%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

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
   AutreThe 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
   LavageThe separated organic phase was washed with saturated NaCl (10 mL)
6. 6
   Séchagedried (Na2SO4)
7. 7
   Autreevaporated

Mode opératoire

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.

Source