Sodium Cyanide → 6-Fluoropyridine-2-carbonitrile

HRID 2099511노트

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HRID 2099511 반응식
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[C-:9]#[N:10].[Na+]>CS(C)=O.CCOC(C)=O>[F:8][C:4]1[N:3]=[C:2]([C:9]#[N:10])[CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 2

HCID 8929Sodium CyanideHCID 739342,6-Difluoropyridine

생성물 1

HCID 142963696-Fluoropyridine-2-carbonitrile

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

2,6 Difluoropyridine (12 g, 100 mmol) was dissolved in DMSO (3 mL) and sodium cyanide (1.3 g, 26 mmol) in DMSO (100 mL) was added dropwise via syringe pump over 16 h. The reaction was then heated at 100° C. for 16 h. The crude mixture was then diluted with EtOAc (500 mL) and washed with a mixture of brine (200 mL) and H2O (500 mL). The organic phase was dried (MgSO4), filtered, and concentrated in vacito. The residue was chromatographed on silica gel eluting with hexanes:EtOAc (4:1) to afford 6-fluoropyridine-2-carbonitrile. MS (ESI) 122.0 (M++H).

후처리

  1. washwashed with a mixture of brine (200 mL) and H2O (500 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacito
  5. customThe residue was chromatographed on silica gel eluting with hexanes:EtOAc (4:1)

출처 및 근거

ORD 기록
ord-516d0035fee54c79901f11e149fc01d7
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569592B2

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