Trimethyl borate → 4-(Difluoromethoxy)benzeneboronic acid

HRID 502856Notes

Reaction equation

[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.C([Mg]Cl)(C)C.[B:17](OC)([O:20]C)[O:18]C>>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([B:17]([OH:20])[OH:18])=[CH:6][CH:5]=1

Participants

Reactant 3

HCID 8470Trimethyl borate

HCID 27370081-(Difluoromethoxy)-4-iodobenzene

HCID 178418918HCID 178418918, compound

Product 1

HCID 230821464-(Difluoromethoxy)benzeneboronic acid

Procedure

In a departure from the procedure described above the compound is prepared from 4-difluoromethoxy-1-iodo-benzene using iPrMgCl to generate the arylmetal compound and trapping this intermediate with trimethyl borate.

Sources & evidence

ORD record: ord-342c09a282554710a5de8d59a6929584
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776830B2

Reaction notes

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