Trimethyl borate → 5-Chloro-2-methoxyphenylboronic acid

HRID 1938378Notes

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

Participants

Reactant 4

HCID 8470Trimethyl borate

HCID 5219352-Bromo-4-chloroanisole

HCID 27826735-Fluoro-2-methoxyphenylboronic acid

HCID 178418339Butyllithium

Product 1

HCID 27357515-Chloro-2-methoxyphenylboronic acidYield 77%

Procedure

This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-chloroanisole (2.00 g, 9.0 mmol, 1.0 equivuiv), n-BuLi (2.5M in hexanes; 3.62 mL, 9.0 mmol, 1.0 equivuiv), and trimethylborate (3.0 mL, 26 mmol, 2.9 equivuiv) to afford 1.30 g (77%) of crude 5-chloro-2-methoxyphenylboronic acid as a white semi-solid. This compound was used in the next reaction with no further purification.

Sources & evidence

ORD record: ord-8a6ee09899864e6d8142bf1269cefcf9
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05693646

Reaction notes

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