Hydrochloric Acid → 4-(2-Hydroxyethyl)phenylboronic acid

To a stirred solution of 4-bromophenethylalcohol (5.00 g, 24.9 mmol) in tetrahydrofuran (80 mL) was added a solution of 1.5 M n-BuLi in hexane (39.8 mL, 59.7 mmol) at −78° C. over 30 min. After 1 hour, a solution of triisopropyl borate (8.61 mL, 37.3 mmol) in tetrahydrofuran (20 mL) was added slowly to the mixture at −78° C. The resulting mixture was warmed to room temperature, and treated with 2 M HCl (100 mL) for 1 hour. This mixture was extracted with dichloromethane and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane/methanol (20:1) to afford 2.61 g (63%) of the title compound as white solids: MS (ESI) m/z 165 [M−H]−, 1H-NMR (CD3OD) δ 2.77 (2H, t, J=7.2 Hz), 3.70 (2H, t, J=7.2 Hz), 7.13-7.19 (2H, m), 7.48-7.64 (2H, m).

1. extractionThis mixture was extracted with dichloromethane
2. dry with materialthe combined organic phase was dried (MgSO4)
3. concentrationconcentrated under reduced pressure
4. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane/methanol (20:1)

ORD record

ord-c5528b3af433479fa0505e2345d7a43f

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06956050B2