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

HRID 1668844노트

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HRID 1668844 반응식
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

참가 물질

3

반응물 2

HCID 109657982-Bromo-5-chloro-3-fluoropyridineHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 220135625-Chloro-3-fluoropyridine-2-carbonitrile수율 66,434.602%

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-42c7eaaa7eb64f4d94df2e6d414b6506
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989469B2

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