2-Bromo-5-chloro-3-fluoropyridine → 5-Chloro-3-fluoropyridine-2-carbonitrile

HRID 1668844ノート

反応式

HRID 1668844 の反応式
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[C:10]([Cu])#[N:11]>>[Cl:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([C:10]#[N:11])=[N:3][CH:4]=1

参加物

3

反応物 2

HCID 109657982-Bromo-5-chloro-3-fluoropyridineHCID 178418546HCID 178418546、化合物

生成物 1

HCID 220135625-Chloro-3-fluoropyridine-2-carbonitrile収率 66,434.602%

反応条件

温度
120 °C

実験手順

2-Bromo-5-chloro-3-fluoropyridine (107 g, 0.5 mmol) and CuCN (55 g, 0.62 mmol) were added to a round bottom flask with a magnetic stirbar. The flask was fitted with a septum and purged with nitrogen for 10 minutes. DMSO (430 mL) was then added by syringe and the resulting mixture stirred at 120° C. for 3 h. The reaction was cooled to room temperature and then poured into a vigorously stirred mixture of EtOAc (1 L) and brine (1 L). The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (15% ethyl ether, 85% hexanes) provided the title compound as an off-white solid (52 g, 67%). The product was characterized by 1H NMR.

後処理

  1. customThe flask was fitted with a septum
  2. custompurged with nitrogen for 10 minutes
  3. additionDMSO (430 mL) was then added by syringe
  4. temperatureThe reaction was cooled to room temperature
  5. additionpoured into a vigorously stirred mixture of EtOAc (1 L) and brine (1 L)
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-42c7eaaa7eb64f4d94df2e6d414b6506
出典データセット
uspto-grants-2011_08
特許番号
US07989469B2

反応ノート

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