Trimethyl borate → (2-Methoxy-5-methylphenyl)boronic acid

HRID 2294472Notes

Reaction equation

F[C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([B:8]([OH:10])[OH:9])[CH:7]=1.Br[C:14]1C=C(C)C=CC=1OC.[Li]CCCC.COB(OC)OC>>[CH3:12][O:11][C:5]1[CH:4]=[CH:3][C:2]([CH3:14])=[CH:7][C:6]=1[B:8]([OH:10])[OH:9]

Participants

Reactant 4

HCID 8470Trimethyl borate

HCID 891432-Bromo-4-methylanisole

HCID 27826735-Fluoro-2-methoxyphenylboronic acid

HCID 178418339Butyllithium

Product 1

HCID 2773485(2-Methoxy-5-methylphenyl)boronic acidYield 96%

Procedure

This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-methylanisole (2.00 g, 9.94 mmol), n-BuLi (2.5M in hexanes; 4.00 mL, 10 mmol), and trimethylborate (3.4 mL, 30 mmol) to afford 1.60 g (96%) of 2-methoxy-5-methylphenylboronic acid which was used without further purification.

Sources & evidence

ORD record: ord-a1ea8391dec348f6a6af0e0923824598
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688810

Reaction notes

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