反応 #1833237

反応方程式

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

溶媒

tetrahydrofuran

ethyl acetate

反応条件

後処理

1. 1
   workup.WAITwas continued for 40 min at 15-20° C
2. 2
   洗浄The organic phase was washed with saturated NaCl (10 mL)
3. 3
   乾燥dried (Na2SO4)
4. 4
   その他evaporated

実験手順

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.

出典