Triisopropyl borate → (4-Methoxy-2-methylphenyl)boronic acid

HRID 1830640Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH3:10].C([Li])CCC.[B:16](OC(C)C)([O:21]C(C)C)[O:17]C(C)C>>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([B:16]([OH:21])[OH:17])=[C:3]([CH3:10])[CH:4]=1

Participants

Reactant 3

HCID 21531Triisopropyl borate

HCID 1179151-Bromo-4-methoxy-2-methylbenzene

HCID 178418339Butyllithium

Product 1

HCID 2773486(4-Methoxy-2-methylphenyl)boronic acid

Procedure

The title compound was prepared by reacting 4-bromo-3-methylanisole (10 g, 0.050 mol) with n-butyl lithium (24 mL of 2.5 M solution in hexane, 0.055 mol) followed by triisopropyl borate (57.7 mL, 47.02 g, 0.25 mol) according to method F to yield 5.7 g (69%) of a white solid: MS (ESI) m/z 313 (2M-H2O—H)−.

Sources & evidence

ORD record: ord-a2de80ae65aa4e61a633cd13130611a4
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

Loading…