Sodium Cyanide → 6-Fluoropyridine-2-carbonitrile

HRID 2099511Notes

Reaction equation

HRID 2099511 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>[F:8][C:4]1[N:3]=[C:2]([C:9]#[N:10])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 739342,6-Difluoropyridine

Product 1

HCID 142963696-Fluoropyridine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-516d0035fee54c79901f11e149fc01d7
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

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