Hydrochloric Acid → 2,4-Bis(methoxymethoxy)phenylboronic acid

Temperature

-78 °C

To a solution of 1-bromo-2,4-bismethoxymethoxybenzene in hexane (250 ml) and tetrahydrofuran (110 ml) was added triisopropyl borate (45 g, 238 mmol), and the mixture was cooled to −78° C. A solution (151 ml, 238 mmol) of 1.58M n-butyllithium in hexane was added dropwise and the mixture was stirred for 5 hr. 1N Hydrochloric acid (240 ml) was added under ice-cooling, and the mixture was stirred for 15 min. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 2,4-bismethoxymethoxyphenylboronic acid (13.6 g, yield 35%).

1. temperaturecooling
2. stirringthe mixture was stirred for 15 min
3. extractionThe reaction mixture was extracted with ethyl acetate
4. washthe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationAfter filtration
7. customthe solvent was evaporated under reduced pressure
8. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

ORD record

ord-f0b433b0f08a4c529744e1e154aa9b62

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977331B1