2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 90413451, compound

Temperature

5 °C

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.

1. additiontreated with isopropylmagnesiumchloride-lithium chloride complex solution (1.3 M; 2.7 mL, 3.5 mmol)
2. stirringstirred for 20 min
3. customThe reaction was quenched by addition of saturated ammonium chloride (NH4Cl; 5 mL)
4. additionmixed with ethyl acetate (20 mL) and saturated NaCl (10 mL)
5. washThe separated organic phase was washed with saturated NaCl (10 mL)
6. dry with materialdried (Na2SO4)
7. customevaporated

ORD record

ord-5fad2adc54fe4cd28ad2edb017ba576c

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149038B2