2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 70665171, compound

Temperature

-78 °C

To a solution of 2-(4-fluorophenyl)furan (1.50 g, 9.25 mmol) in dry tetrahydrofuran (100 mL) was added a solution of n-BuLi (4.4 mL, 2.5M solution in hexane) dropwise with stirring at −78° C. under nitrogen. The resulting solution was warmed slowly to −40° C. over 45 min and stirred at this temperature for another 30 min. The mixture was cooled again below −78° C. followed by dropwise addition of 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane (3.42 g, 18.38 mmol). After warming to room temperature, the mixture was quenched with NH4Cl (aq) and extracted with ethyl acetate (3×80 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the residue (1.20 g crude), which was used to the next step without further purification.

1. temperatureThe resulting solution was warmed slowly to −40° C. over 45 min
2. stirringstirred at this temperature for another 30 min
3. temperatureThe mixture was cooled again below −78° C.
4. temperatureAfter warming to room temperature
5. customthe mixture was quenched with NH4Cl (aq)
6. extractionextracted with ethyl acetate (3×80 mL)
7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto give the residue (1.20 g crude), which
11. customwas used to the next step without further purification

ORD record

ord-4f3ac8b1289a4656ae22bc94302443f4

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08912188B2