Water → Phenylboronic Acid

In an Ar atmosphere, the crystals of 2-(4-bromophenyl)-naphthalene obtained in Synthesis Step C1-3, 10 g, and 500 mL of anhydrous tetrahydrofuran were put into a 1-L flask, and then 22 mL of a 1.6 mol/L n-BuLi solution in hexane was added dropwise at −60° C. over 30 minutes. Thirty minutes later, 7 g of triisopropyl borate was added dropwise, and then the reaction was allowed to proceed overnight with no temperature control. After the completion of the reaction, 100 mL of water was added dropwise, and the obtained solution was subjected to extraction with 2 L of toluene and separated. The isolated organic layer was concentrated, the residue was recrystallized, and the crystals were collected by filtration and dried. In this way, a phenylboronic acid derivative was obtained as a white solid weighing 5 g.

1. customwere put into a 1-L flask
2. additionwas added dropwise
3. extractionthe obtained solution was subjected to extraction with 2 L of toluene
4. customseparated
5. concentrationThe isolated organic layer was concentrated
6. customthe residue was recrystallized
7. filtrationthe crystals were collected by filtration
8. customdried

ORD record

ord-eb3dcf95832e4b9ca662c0d45428fe92

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09324952B2