Hydrochloric Acid → (5-(Ethoxymethoxy)-2-ethylphenyl)boronic acid

Temperature

-78 °C

12 g (49 mmol) of 1-bromo-2-ethyl-5-ethoxymethoxybenzene are placed in 200 ml of dry THF in a round-bottomed flask and under a stream of nitrogen. The reaction medium is cooled to −78° C. and 23 ml (58 mmol) of 2.5M n-butyllithium in hexane are added dropwise. 20 minutes later, 13.6 ml (59 mmol) of triisopropyl borate are added slowly. Stirring is continued for 1 hour at −78° C. The mixture is then poured into a solution of water and hydrochloric acid and is then extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (50/50). After evaporating off the solvents, 6.7 g (65%) of the expected product are obtained in the form of white crystals.

1. extractionis then extracted with ethyl acetate
2. dry with materialThe organic phase is dried over magnesium sulfate
3. filtrationfiltered
4. customevaporated
5. customThe residue obtained
6. customis purified by chromatography on a column of silica
7. washeluted with a mixture of heptane and ethyl acetate (50/50)
8. customAfter evaporating off the solvents, 6.7 g (65%) of the expected product
9. customare obtained in the form of white crystals

ORD record

ord-d6fd86ff902941e38ed4258c2270b3d2

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06924400B2