Hydrochloric Acid → 4'-Pentyl-4-biphenylboronic Acid (contains varying amounts of Anhydride)

Temperature

-78 °C

4-Bromo-4′-pentylbiphenyl (3 g, 9.9 mmol) was added in one portion to Mg (0.27 g, 11.1 mmol), treated with I2, in THF (40 mL). The mixture was heated at reflux for 3 h, cooled to −78° C. and trimethyl borate (2.06 g, 19.8 mmol) was added dropwise. The mixture was warmed to room temperature over 1 h, acidified with HCl (2 M, 50 mL), extracted with Et2O (3×50 mL). The combined ethereal washes were extracted with NaOH (100 mL, 1 M). The aqueous phase was acidified with concentrated HCl, extracted with Et2O (3×50 mL), dried (MgSO4) and the solvent removed under reduced to give the title compound (2.07 g, 78%) as an off white powder.

1. temperatureThe mixture was heated
2. temperatureat reflux for 3 h
3. temperatureThe mixture was warmed to room temperature over 1 h
4. extractionextracted with Et2O (3×50 mL)
5. extractionThe combined ethereal washes were extracted with NaOH (100 mL, 1 M)
6. extractionextracted with Et2O (3×50 mL)
7. dry with materialdried (MgSO4)
8. customthe solvent removed

ORD record

ord-35e97ac7a0a546958f8063dea8c81ab0

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703978B2