4-Bromo-2,6-difluorobenzonitrile → 4-Bromo-2-fluoro-6-methoxybenzonitrile

HRID 922388ノート

反応式

HRID 922388 の反応式
[Br:1][C:2]1[CH:9]=[C:8](F)[C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1.[CH3:12][O-:13].[Na+]>C1COCC1>[Br:1][C:2]1[CH:9]=[C:8]([O:13][CH3:12])[C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1

参加物

4

反応物 2

HCID 27569164-Bromo-2,6-difluorobenzonitrileHCID 10942334Sodium Methoxide

生成物 1

HCID 574422094-Bromo-2-fluoro-6-methoxybenzonitrile収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-bromo-2,6-difluorobenzonitrile (1, 15.0 g, 69 mmol) in THF (100 mL) at 0° C. was slowly added sodium methoxide (25% wt in methanol, 14.9 g, 69 mmol) and the mixture was stirred at room temperature for 16 h. The mixture was concentrated and partitioned between dichloromethane (500 mL) and water (250 mL). The organic extracts were dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with ethyl acetate in hexane (0-100%) to afford the title compound (15.2 g, 99%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.01-6.99 (m, 1H), 6.94 (s, 1H), 3.96 (s, 1H).

後処理

  1. customat 0° C.
  2. concentrationThe mixture was concentrated
  3. custompartitioned between dichloromethane (500 mL) and water (250 mL)
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with ethyl acetate in hexane (0-100%)

出典と根拠

ORDレコード
ord-f6637e0155f24b228262c086adfe4b91
出典データセット
uspto-grants-2016_03
特許番号
US09278940B2

反応ノート

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