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

HRID 578749

반응식

HRID 578749 반응식
[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]

참가 물질

3

반응물 1

HCID 71187258Boronic acid, B-[4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3,5-difluorophenyl]-

생성물 1

HCID 447547723,5-Difluoro-4-(hydroxymethyl)phenylboronic acid

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
40 °C

실험 절차

[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.

후처리

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

출처 및 근거

ORD 기록
ord-bdb04ad6ea5f41c997219a58bf2c93f2
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040691B2

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