Trimethyl borate → [4-(Difluoromethyl)phenyl]boronic acid

HRID 1041941Notes

Reaction equation

HRID 1041941 reaction equation
[F:1][CH:2]([F:10])[C:3]1[CH:8]=[CH:7][C:6](I)=[CH:5][CH:4]=1.C([Mg]Cl)(C)C.[B:16](OC)([O:19]C)[O:17]C>>[F:1][CH:2]([F:10])[C:3]1[CH:8]=[CH:7][C:6]([B:16]([OH:19])[OH:17])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 8470Trimethyl borateHCID 463117371-(Difluoromethyl)-4-iodobenzeneHCID 178418918HCID 178418918, compound

Product 1

HCID 20777176[4-(Difluoromethyl)phenyl]boronic acid

Procedure

In a departure from the procedure described above the compound is prepared from 4-difluoromethyl-1-iodo-benzene (prepared from 4-iodobenzaldehyde using diethylaminosulfurtrifluoride (DAST) in dichloromethane) using iPrMgCl to generate the arylmetal compound and trapping this intermediate with trimethyl borate.

Sources & evidence

ORD record
ord-1b9daa997eee47b2a21ac3656d5a8e5d
Source dataset
uspto-grants-2013_10
Patent number
US08557782B2

Reaction notes

Loading…