Trimethyl borate → (3-Chloro-2-methoxyphenyl)boronic acid

HRID 2121785Notes

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

Participants

Reactant 4

HCID 8470Trimethyl borate

HCID 27826735-Fluoro-2-methoxyphenylboronic acid

HCID 234336171-Bromo-3-chloro-2-methoxybenzene

HCID 178418339Butyllithium

Product 1

HCID 15766875(3-Chloro-2-methoxyphenyl)boronic acidYield 91%

Procedure

This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-6-chloroanisole (0.71 g, 3.2 mmol), n-BuLi (2.5 M hexanes; 1.28 mL, 3.2 mmol), and trimethylborate (1.09 mL, 9.6 mmol) to afford 0.55 g (91%) of 3-chloro-2-methoxyphenylboronic acid which was used without further purification.

Sources & evidence

ORD record: ord-e6993d9b85a04892ad306e6a87751da8
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696459B1

Reaction notes

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