Hydrochloric Acid → 5-Formylfuran-2-boronic acid

Temperature

-78 °C

An amount of 1.0 g (4.1 mmol) of 4-bromo-2-(diethoxymethyl)furan, is dissolved in ether (15 mL) and cooled to −78° C. To this is added 4.3 mL (6.02 mmol) of sec-butyllithium. After stirring at −78° C. for 30 minutes, triisopropyl borate (1.10 mL, 5.01 mmol) is added dropwise. The mixture is stirred at −78° C. for 1.5 hours and brought to room temperature for 2 hours. The mixture is hydrolyzed with 2N HCl and stirred at room temperature for 1 hour. The ether layer is separated and the water layer is washed once more with ether. The combined ether layers is washed once with brine and dried with sodium sulfate. Evaporated to give 563 mg of the boronic acid as dark oil.

1. stirringThe mixture is stirred at −78° C. for 1.5 hours
2. waitbrought to room temperature for 2 hours
3. stirringstirred at room temperature for 1 hour
4. customThe ether layer is separated
5. washthe water layer is washed once more with ether
6. washThe combined ether layers is washed once with brine
7. dry with materialdried with sodium sulfate
8. customEvaporated

ORD record

ord-4bcd197f139740dab06f6230d46a218d

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07713994B2