反応 #1833238

反応方程式

NH4Cl

5-Bromo-6-chloro-2,2-difluorobenzo[d][1,3]dioxole

isopropylmagnesium lithium chloride

NaCl

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

→

title compound

収率 101.8%

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

収率 101.8%

溶媒

tetrahydrofuran

ethyl acetate

反応条件

後処理

1. 1
   workup.WAITwas continued for 45 min at 10-15° 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

5-Bromo-6-chloro-2,2-difluorobenzo[d][1,3]dioxole (1.0 g, 3.7 mmol) was dissolved in dry tetrahydrofuran (7 mL), cooled to 0-5° C. and treated in portions with isopropylmagnesium lithium chloride (1.3 M; 3.0 mL, 3.9 mmol). After 30 min, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (730 mg, 4.0 mmol) was added, and stirring was continued for 45 min at 10-15° C. Saturated NH4Cl (10 mL) was added and the mixture was shaken with ethyl acetate (20 mL) and saturated NaCl (10 mL). The organic phase was washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated to give the title compound as a white solid (1.2 g, qt): 1H NMR (400 MHz, DMSO-d6) δ 7.64 (s, 1H), 7.53 (s, 1H), 1.30 (s, 12H); 19F NMR (376 MHz, DMSO-d6) δ −48.97 (s); EIMS m/z 318.

出典