11-Bromo-1-undecanol → 4-(11'-Hydroxyundecyl)carboxyphenylboronic acid

Temperature

60 °C

A mixture of 4-carboxyphenylboronic acid (1.0 grams), potassium hydrogen carbonate (2.01 g), 11-bromo-1-undecanol, and N,N-dimethylformamide (60 mL) was heated at 60° C. under a nitrogen atmosphere for 18 hours. After the heating period, the mixture was allowed to cool to room temperature. The mixture was then filtered and the filtrate was concentrated on a rotary evaporator. The concentrated filtrate was diluted with ethyl acetate (500 mL) and the ethyl acetate was washed successively with saturated aqueous sodium bicarbonate (3×300 mL), followed by saturated aqueous sodium chloride (300 mL). After drying over sodium sulfate, the ethyl acetate extract was concentrated on a rotary evaporator and dried under reduced pressure to afford 2.2 grams of the desired product as a light yellow viscous oil that solidified upon standing to a white powder.

1. temperatureto cool to room temperature
2. filtrationThe mixture was then filtered
3. concentrationthe filtrate was concentrated on a rotary evaporator
4. additionThe concentrated filtrate was diluted with ethyl acetate (500 mL)
5. washthe ethyl acetate was washed successively with saturated aqueous sodium bicarbonate (3×300 mL)
6. dry with materialAfter drying over sodium sulfate
7. extractionthe ethyl acetate extract
8. concentrationwas concentrated on a rotary evaporator
9. customdried under reduced pressure

ORD record

ord-6881f7df2783405183353d4abbaf289b

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06858592B2