Sodium Cyanide → 6-Fluoropyridine-2-carbonitrile

HRID 2041202노트

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HRID 2041202 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>[C:9]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1)#[N:10]

참가 물질

5

반응물 2

HCID 8929Sodium CyanideHCID 739342,6-Difluoropyridine

생성물 1

HCID 142963696-Fluoropyridine-2-carbonitrile수율 22.3%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

Dissolve 2,6-difluoropyridine (12 g, 104.2 mmol) in anhydrous DMSO (5 mL). Add a solution of sodium cyanide (1.3 g, 26.53 mmol) in DMSO (60 mL) over 12 h using a syringe pump. Heat the mixture to 100° C. overnight. Cool to ambient temperature, dilute with EtOAc (500 mL), and wash with brine. Dry the organic phase over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 4:1) to give the desired intermediate as a solid (723 mg, 22%). GC-MS m/z: 122 (M+).

후처리

  1. temperatureCool to ambient temperature
  2. washwash with brine
  3. dry with materialDry the organic phase over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 4:1)

출처 및 근거

ORD 기록
ord-9218186c655044f6ab8129494ddaa55b
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580780B2

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