Boronic acid, B-[4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3,5-difluorophenyl]- → 3,5-Difluoro-4-(hydroxymethyl)phenylboronic acid

HRID 578749

Reaction equation

[Si]([O:8][CH2:9][C:10]1[C:15]([F:16])=[CH:14][C:13]([B:17]([OH:19])[OH:18])=[CH:12][C:11]=1[F:20])(C(C)(C)C)(C)C>C(O)(=O)C>[F:16][C:15]1[CH:14]=[C:13]([B:17]([OH:18])[OH:19])[CH:12]=[C:11]([F:20])[C:10]=1[CH2:9][OH:8]

Participants

Conditions

Temperature: 40 °C

Procedure

[4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3,5-difluorophenyl]boronic acid (19.3 g, 63.9 mmol; crude material, prepared by the method of Hattori, Bioorg. Med. Chem. 2006, 14, 3258-3262) was dissolved in 400 mL aqueous acetic acid (66%) and stirred at 40° C. for 5 h. The solution was then evaporated under reduced pressure, and the residue was purified by flash chromatography over silica gel (gradient elution from 0% to 2% methanol in dichloromethane) to give 3.46 g (25% of th., LC-MS purity 87%) of the title compound.

Workup

customcrude material, prepared by the method of Hattori, Bioorg
customThe solution was then evaporated under reduced pressure
customthe residue was purified by flash chromatography over silica gel (gradient elution from 0% to 2% methanol in dichloromethane)

Sources & evidence

ORD record: ord-bdb04ad6ea5f41c997219a58bf2c93f2
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040691B2

Linked notes

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