Sodium Cyanide → 6-Fluoropyridine-2-carbonitrile

HRID 2041202Notes

Reaction equation

HRID 2041202 reaction equation
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]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 739342,6-Difluoropyridine

Product 1

HCID 142963696-Fluoropyridine-2-carbonitrileYield 22.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-9218186c655044f6ab8129494ddaa55b
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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