Water → 5-Bromo-3-methylpyridine-2-carbonitrile

HRID 2357527Notes

Reaction equation

HRID 2357527 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[Cu][C:11]#[N:12].O>CN(C=O)C>[Br:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([C:11]#[N:12])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8176802,5-Dibromo-3-methylpyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 207750075-Bromo-3-methylpyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 2,5-dibromo-3-methylpyridine (20.17 g, 80.4 mmol) and copper(I) cyanide (7.24 g, 80.8 mmol) in 200 mL DMF was heated to 115° C. overnight. The reaction mixture was cooled to 25° C. and poured into 600 mL of H2O. The solid was filtered, washed with copious amounts of H2O. The filtrate was extracted with EtOAc (4×) and the combined organic layers were washed with H2O and dried over Na2SO4. The solution was filtered, evaporated onto silica gel and purified by flash chromatography eluting with EtOAc:hexane (0:1→1:9) to give the title compound as a white solid. MS m/z: 197.0 [M+1].

Workup

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. filtrationThe solid was filtered
  3. washwashed with copious amounts of H2O
  4. extractionThe filtrate was extracted with EtOAc (4×)
  5. washthe combined organic layers were washed with H2O
  6. dry with materialdried over Na2SO4
  7. filtrationThe solution was filtered
  8. customevaporated onto silica gel
  9. custompurified by flash chromatography
  10. washeluting with EtOAc:hexane (0:1→1:9)

Sources & evidence

ORD record
ord-13b02afa25e044f4afc5c246dbf84619
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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