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

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 (2.5M in 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.