Hydrochloric Acid → (3-Methoxyphenyl)boronic acid

n-Butyllithium in n-hexane (925.0 mL, 1.59 M) was added dropwise to a mixture of THF (1,000 mL) and 1-bromo-3-methoxybenzene (T-1) (250.0 g, 1.34 mol) at −70° C. under an atmosphere of nitrogen. After the addition had been completed, the reaction mixture was stirred at the same temperature for 1 hour. Triisopropyl borate (300.9 g, 1.60 mol) was added dropwise, and then the mixture was warmed slowly to room temperature. The stirring was continued at room temperature for 18 hours, and the reaction mixture was poured into 6M-hydrochloric acid. The mixture was extracted with ethyl acetate (500 mL) four times, and the organic layer was washed with water. After the organic layer had been dried over anhydrous magnesium sulfate, the organic solvent was distilled off under reduced pressure. The residue was sufficiently washed with heptane to leave colorless solids (156.1 g) of 3-methoxyphenylboronic acid (T-2).

1. additionAfter the addition
2. waitThe stirring was continued at room temperature for 18 hours
3. extractionThe mixture was extracted with ethyl acetate (500 mL) four times
4. washthe organic layer was washed with water
5. dry with materialAfter the organic layer had been dried over anhydrous magnesium sulfate
6. distillationthe organic solvent was distilled off under reduced pressure
7. washThe residue was sufficiently washed with heptane

ORD record

ord-cea886328f7b4c4bb6d72f2c1edcb280

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394468B2