Hydrochloric Acid → Pyren-1-ylboronic acid

Temperature

0 °C

An excess of 1.6 M n-BuLi in hexane (50 mL, 80 mmol) was added to a solution of 1-bromopyrene (20.4 g, 72.6 mmol) in 500 ml dry tetrahydrofuran at −78° C. under N2. The reaction mixture was then maintained at 0° C. for 1 h before cooling to −78° C. Trimethyl borate (10.4 g, 100 mmol) was added dropwise; the solution was then warmed slowly to room temperature and stirred for 24 h. 2N HCl (150 ml) was added and then the mixture was stirred for a further 1 h. The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuo, and the residue was crystallized (n-hexane) to give the pyren-1-ylboronic acid 12.5 g as a yellow solid (70%)

1. temperaturebefore cooling to −78° C
2. temperaturethe solution was then warmed slowly to room temperature
3. stirringthe mixture was stirred for a further 1 h
4. extractionThe reaction mixture was extracted with ethyl acetate and water
5. dry with materialdried with anhydrous magnesium sulfate
6. customthe solvent was evaporated in vacuo
7. customthe residue was crystallized (n-hexane)

ORD record

ord-085b29ffaf174e9995da5d9c6730ee16

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260363B2