2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 90413696, compound

Temperature

-25 °C

5-Bromo-4-chloro-2,2-difluorobenzo[d][1,3]dioxole (1.0 g, 3.7 mmol) was dissolved in dry tetrahydrofuran (12 mL), cooled to −20 to −30° C. and treated in portions with isopropylmagnesium chloride-lithium chloride complex solution (1.3 M; 3.1 mL, 4.1 mmol). After 90 min at −20 to 0° C., 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (830 μL, 750 mg, 4.1 mmol) was added, and stirring was continued at 0-20° C. for 90 min. The reaction was quenched by addition of saturated NH4Cl (10 mL), and the mixture was extracted with ethyl acetate (30 mL). The aqueous phase was extracted again with ethyl acetate (15 mL), and the combined organic phases were washed with saturated NaCl (15 mL), dried (Na2SO4) and evaporated to give the title compound as a white solid (1.2 g, ca. 100%): 1H NMR (400 MHz, CDCl3) δ 7.52 (d, J=8.1 Hz, 1H), 6.99-6.94 (m, 1H), 1.36 (s, 12H); 19F NMR (376 MHz, CDCl3) δ −49.62 (s); EIMS m/z 318.

1. additiontreated in portions with isopropylmagnesium chloride-lithium chloride complex solution (1.3 M; 3.1 mL, 4.1 mmol)
2. waitwas continued at 0-20° C. for 90 min
3. customThe reaction was quenched by addition of saturated NH4Cl (10 mL)
4. extractionthe mixture was extracted with ethyl acetate (30 mL)
5. extractionThe aqueous phase was extracted again with ethyl acetate (15 mL)
6. washthe combined organic phases were washed with saturated NaCl (15 mL)
7. dry with materialdried (Na2SO4)
8. customevaporated

ORD record

ord-56002e9ab91441b5be1d51d2814348b8

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149038B2