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

HRID 1519441ノート

反応式

HRID 1519441 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-bed19ba507604c108f1b5a766a722d92
出典データセット
uspto-grants-2015_07
特許番号
US09073878B2

反応ノート

読み込み中…