Triethyl borate → n-Tetradecylboronic acid

Temperature

-20 °C

To a stirred solution of tetradecylmagnesium chloride (50 ml, 1M in THF) was added at −20° C. to THF (50 ml) followed by triethyl borate (10.2 ml, 60 mmol). The reaction mixture was stirred briefly at −20° C., and warmed up slowly over 3 hours to room temperature. Most of the solvent was removed on rotary evaporator and the concentrated mixture was poured into water (300 ml) and pH of the mixture was adjusted to about pH 4 using 12N hydrochloric acid. After being stirred for 10 hours, precipitated tetradecylboronic acid was isolated by filtration, washed three times with water and dried with air overnight. The dried white solid was washed with cold hexane to remove a trace of tetradecane and dried with air to yield 11.3 g (93%) of n-tetradecylboronic acid.

1. temperaturewarmed up slowly over 3 hours to room temperature
2. customMost of the solvent was removed on rotary evaporator
3. additionthe concentrated mixture was poured into water (300 ml)
4. stirringAfter being stirred for 10 hours
5. customprecipitated tetradecylboronic acid
6. customwas isolated by filtration
7. washwashed three times with water
8. customdried with air overnight
9. washThe dried white solid was washed with cold hexane
10. customto remove a trace of tetradecane
11. customdried with air

ORD record

ord-a30f39bfaf3449188de1ea42aa199ccb

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106117B2