Trimethyl borate → 2,5-Dimethoxyphenylboronic acid

HRID 2294467Notes

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.BrC1C=[C:18]([O:20]C)C=CC=1OC.[Li]CCCC.COB(OC)OC>>[CH3:12][O:11][C:5]1[CH:4]=[CH:3][C:2]([O:20][CH3:18])=[CH:7][C:6]=1[B:8]([OH:10])[OH:9]

Participants

Reactant 4

HCID 8470Trimethyl borate

HCID 91353Benzene, 2-bromo-1,4-dimethoxy-

HCID 27826735-Fluoro-2-methoxyphenylboronic acid

HCID 178418339Butyllithium

Product 1

HCID 27343422,5-Dimethoxyphenylboronic acidYield 99%

Procedure

This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 1-bromo-2,5-dimethoxybenzene (2.00 mL, 13.3 mmol), n-BuLi (2.5M in hexanes; 5.34 mL, 13.3 mmol), and trimethylborate (4.5 mL, 40 mmol) to afford 2.43 g (99%) of 2,5-dimethoxyphenylboronic acid which was used without further purification.

Sources & evidence

ORD record: ord-dc097e31ae5a4c4992f83e3cbeedb61f
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688810

Reaction notes

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