2,4-Difluorobenzonitrile → 4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile

HRID 346475

반응식

HRID 346475 반응식
F[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Na].[NH:12]1[CH:16]=[N:15][CH:14]=[N:13]1>C1COCC1.CN(C=O)C>[F:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[CH:9]=1

참가 물질

5

반응물 2

HCID 775452,4-DifluorobenzonitrileHCID 454898221h-1,2,4-Triazole sodium salt

생성물 1

HCID 210698804-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile수율 18.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol), dissolved in THF (20 mL) and DMF (40 mL), was added 1,2,4-triazole sodium salt (6.3 g, 70 mmol) and the resulting mixture stirred at 90° C. for 3 h, after which it was filtered and concentrated. The remaining residue was adsorbed onto silica gel and purified by flash column chromatography eluting with 0%–30% ethyl acetate/hexanes to give the title compound as colorless needles (2.46 g, 18% yield). 1H NMR (500 MHz, CDCl3) δ ppm: 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28–7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13.

후처리

  1. filtrationafter which it was filtered
  2. concentrationconcentrated
  3. custompurified by flash column chromatography
  4. washeluting with 0%–30% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-1e4f5502f8c7454f936d958a0706afed
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173022B2

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