Propionitrile → 3-Bromo-5-chloropyridine-2-carbonitrile

HRID 1526547Notes

Reaction equation

HRID 1526547 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[C:10]([Br:11])=[CH:9][C:8]([Cl:12])=[CH:7][N:6]=1.C(#N)CC>>[Br:11][C:10]1[C:5]([C:2]#[N:3])=[N:6][CH:7]=[C:8]([Cl:12])[CH:9]=1

Participants

4

Reactant 3

HCID 7854PropionitrileHCID 110001622,3-Dibromo-5-chloropyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 225912463-Bromo-5-chloropyridine-2-carbonitrileYield 83.2%

Procedure

A microwave vial was charged with copper (I) cyanide (1.089 g, 12.16 mmol), 2,3-dibromo-5-chloropyridine (3 g, 11.06 mmol), and propionitrile (15 mL). The vial was capped and irradiated in a microwave reactor at 150° C. for 2.5 hours. The solution was concentrated, diluted with DCM (25 mL), and filtered. The filtrate was concentrated, and the residue was purified by silica gel chromatography, eluting with 0-30% EtOAc in heptanes, to afford the title compound (2 g, 9.20 mmol). MS m/z=219 (M+H)+.

Workup

  1. customThe vial was capped
  2. customirradiated in a microwave reactor at 150° C. for 2.5 hours
  3. concentrationThe solution was concentrated
  4. additiondiluted with DCM (25 mL)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 0-30% EtOAc in heptanes

Sources & evidence

ORD record
ord-d3e65548e10a4ae8aeb8dc688483232b
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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