Sodium Cyanide → 2-(6-Bromopyridin-3-yl)acetonitrile
反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][N:3]=1.[C-:10]#[N:11].[Na+]>CCO>[Br:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][C:10]#[N:11])=[CH:6][CH:7]=1参加物
4
実験手順
A solution of 2-bromo-5-(bromomethyl)pyridine (example 40e) (6 g, 24 mmol) and NaCN (1.42 g, 29 mmol) in absolute EtOH (50 mL) was heated at 80° C. for 8 h. The mixture was then cooled to room temperature then evaporated. The residue was suspended in water and extracted with EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel (5-30% EtOAc/hexanes) to give 2.89 g (63%) of 2-(6-Bromopyridin-3-yl)acetonitrile. 1H NMR (400 MHz, dMSO): δ 4.07 (s, 2H), 7.66-7.68 (d, 1H), 7.72-7.73 (dd, 1H), 8.36-8.37 (d, 1H).
後処理
- customthen evaporated
- extractionextracted with EtOAc
- washThe organic phase was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- customThe residue was purified by chromatography on silica gel (5-30% EtOAc/hexanes)
出典と根拠
- ORDレコード
- ord-1e6462edef2940cbab71ba63a4260208
- 出典データセット
- uspto-grants-2010_11
- 特許番号
- US07842324B2
反応ノート
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