Réaction #1833237

Équation de réaction

NH4Cl

2,2-Difluoro-5-iodo-6-methoxybenzo[d][1,3]dioxole

isopropylmagnesium lithium chloride

NaCl

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

→

title compound

2-(2,2-Difluoro-6-methoxybenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Solvants

tetrahydrofuran

ethyl acetate

Conditions de réaction

Traitement

1. 1
   workup.WAITwas continued for 40 min at 15-20° C
2. 2
   LavageThe organic phase was washed with saturated NaCl (10 mL)
3. 3
   Séchagedried (Na2SO4)
4. 4
   Autreevaporated

Mode opératoire

2,2-Difluoro-5-iodo-6-methoxybenzo[d][1,3]dioxole (1.6 g, 5.0 mmol) was dissolved in dry tetrahydrofuran (15 mL), cooled to 0-5° C. and treated in portions with isopropylmagnesium lithium chloride (1.3 M; 4.1 mL, 5.3 mmol). After 50 min, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.0 g, 5.4 mmol) was added and stirring was continued for 40 min at 15-20° C. The mixture was treated with saturated NH4Cl (10 mL) and then mixed with saturated NaCl (10 mL) and ethyl acetate (20 mL). The organic phase was washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated to give title compound as a thick oil which was used without further purification (1.4 g, 89%): 1H NMR (400 MHz, CDCl3) δ 7.35 (s, 1H), 6.65 (s, 1H), 3.81 (s, 3H), 1.34 (s, 12H); 19F NMR (376 MHz, CDCl3) δ −50.17 (s); EIMS m/z 314.

Source